[ CAS No. 2387-23-7 ] {[proInfo.proName]}

Name: 2387-23-7|1,3-Dicyclohexylurea|95%
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Quality Control of [ 2387-23-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 2387-23-7 ]

Product Details of [ 2387-23-7 ]

CAS No. :	2387-23-7	MDL No. :	MFCD00003829
Formula :	C₁₃H₂₄N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ADFXKUOMJKEIND-UHFFFAOYSA-N
M.W :	224.34	Pubchem ID :	4277
Synonyms :	N,N'-Dicyclohexylurea;NSC 17013;DCU

Calculated chemistry of [ 2387-23-7 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.92
Num. rotatable bonds :	4
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	66.57
TPSA :	41.13 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.47 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.68
Log Po/w (XLOGP3) :	3.09
Log Po/w (WLOGP) :	2.95
Log Po/w (MLOGP) :	2.56
Log Po/w (SILICOS-IT) :	2.01
Consensus Log Po/w :	2.66

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.91
Solubility :	0.274 mg/ml ; 0.00122 mol/l
Class :	Soluble
Log S (Ali) :	-3.62
Solubility :	0.0536 mg/ml ; 0.000239 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.81
Solubility :	0.345 mg/ml ; 0.00154 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.07

Safety of [ 2387-23-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2387-23-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 2387-23-7 ]
Downstream synthetic route of [ 2387-23-7 ]

[ 2387-23-7 ] Synthesis Path-Upstream 1~10

1
[ 2387-23-7 ]
[ 538-75-0 ]

Yield	Reaction Conditions	Operation in experiment
99.5%	With bis(trichloromethyl) carbonate In 1-methyl-pyrrolidin-2-one at 30 - 40℃; for 6 h; Autoclave	1000 ml of NMP and 100 g of DCU were added to the autoclave at 30 ° C, stirred well, 200 g of BTC was added, and thenAdding the composite catalyst (the dosage ratio of DCU and composite catalyst is 1: 0.0001), raising the temperature to 40 DEG C,Reaction 6h, after the completion of the reaction, add triethylamine to adjust the pH to 7.5, hot filter, atmospheric distillation of the solvent, and then vacuum distillationDistillate, collecting 155 ± 1 ° C distillate, in the oven vacuum drying to obtain a white crystalline solid DCC.
88%	With benzenesulfonyl chloride In dichloromethane at 40℃; for 3 h;	Dicyclohexylurea (448.5, 2.0 mol) was added to dichloromethane (1600 ml).Maintain 40 ° C ± 2 ° C, slowly add 430 g of benzenesulfonyl chloride, drop, continue to stir for 3 h,Cool to 0-5 ° C, slowly add 5percent sodium hydroxide solution,Adjust pH=7, separate the organic layer, wash twice with water (800ml).Drying anhydrous sodium sulfate for 5 h, filtering, and distilling off the dichloromethane to recover dichloromethane.Switch to vacuum distillation and collect 155 ° C - 159 ° C / mmHg fraction,DCC (216.5 g, yield 88.0percent) was obtained.
82%	With trichlorophosphate In chloroform; water at 55 - 60℃; for 2 h;	The 5 kg N,N'-dicyclohexylurea raw material was placed in 10 kg of water and stirred for 40 min. The DCU was centrifuged and then dried in an oven at 110-120 ° C until the water was less than 0.5percent 175 g of trichloromethane was added to a three-necked flask, and 40.0 g of dried DCU was added with stirring. Weigh 30g of phosphorus oxychloride and add to a 250 mL dropping funnel. Stirring to the three-necked flask drop of phosphorus oxychloride, 30min added. After the addition, the reaction is maintained between 55-60 ° C for 2 hours. The reaction solution was poured into a dropping funnel. The reaction was filtered while hot, and the solid component was washed twice with 20 g of trichloromethane. The filtrate was allowed to stand for 1.5 hours and divided into an organic layer and an aqueous layer containing phosphate and sodium chloride. The water layer and the intermediate layer are filtered. The filtrate is allowed to stand for more than 12 hours. Take the supernatant as the water for the configuration of the lye. The solid components were washed twice with 20 g of trichloromethane and the organic layers of the washings were combined and the chloroform was separated by distillation. The components were collected by distillation under reduced pressure at 122-124 ° C / 6 mmHg to obtain a DCC product, As a raw material solvent reuse. 30 g of DCC was obtained in a yield of 82percent, and the purity of DCC as determined by gas chromatography was 99.5percent

78%

With iodine; triethylamine; triphenylphosphine In dichloromethane for 1 h; Sonication

General procedure: To a solution of 0.0844 g iodine (0.33 mmol) and 0.0872 g triphenylphosphine (0.33 mmol) in 2 cm3 CH2-Cl2 was added a solution of thiourea or urea(0.275 mmol) and 0.0701 g triethylamine (0.69 mmol) in2 cm3 CH2Cl2 under sonication. The reaction mixture was further sonicated until completion of the reaction as indicated by TLC. The crude mixture was concentrated under reduced pressure then purified by column chromatography using hexane to give the carbodiimide (see supporting information for characterization data of all products).

Reference： [1] Tetrahedron Letters, 1996, vol. 37, # 39, p. 7047 - 7048
[2] Patent: CN105503656, 2016, A, . Location in patent: Paragraph 0027; 0028
[3] Synthesis, 1981, # 5, p. 373 - 374
[4] Bulletin de la Societe Chimique de France, 1981, vol. <II> 2, # 9-10, p. 361 - 364
[5] Patent: CN108424383, 2018, A, . Location in patent: Paragraph 0022; 0030; 0031
[6] Patent: CN104262200, 2016, B, . Location in patent: Paragraph 0038-0043
[7] Synthesis, 1983, # 2, p. 139 - 141
[8] Monatshefte fur Chemie, 2016, vol. 147, # 11, p. 1945 - 1949
[9] Zeitschrift fuer Chemie (Stuttgart, Germany), 1981, vol. 21, # 1, p. 25 - 27
[10] Biochemical Journal, 1957, vol. 65, p. 197,199[11] Biochemical Preparations, 1960, vol. 7, p. 5,11
[12] Justus Liebigs Annalen der Chemie, 1951, vol. 571, p. 83,85
[13] Justus Liebigs Annalen der Chemie, 1958, vol. 612, p. 11,17
[14] DRP/DRBP Org.Chem.,
[15] Patent: US2479498, 1946, ,
[16] Synthesis, 1980, # 9, p. 755 - 757
[17] Synthesis, 1987, # 5, p. 520 - 523
[18] Dalton Transactions, 2013, vol. 42, # 28, p. 10271 - 10276
[19] Journal of the American Chemical Society, 2018, vol. 140, # 5, p. 1627 - 1631
[20] Organic Process Research and Development, 2018, vol. 22, # 3, p. 399 - 402
[21] Patent: US2479498, 1946, ,
[22] DRP/DRBP Org.Chem.,

2
[ 931-53-3 ]
[ 108-91-8 ]
[ 2387-23-7 ]
[ 538-75-0 ]

Reference： [1] Chemical Communications, 1997, # 4, p. 347 - 348

3
[ 2387-23-7 ]
[ 603-35-0 ]
[ 538-75-0 ]
[ 791-28-6 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 1, p. 373 - 376
[2] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 1, p. 373 - 376

4
[ 2387-23-7 ]
[ 931-53-3 ]
[ 2666-80-0 ]
[ 538-75-0 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1983, vol. 325, # 5, p. 787 - 802

5
[ 2387-23-7 ]
[ 98-59-9 ]
[ 538-75-0 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1956, p. 1360

6
[ 64-17-5 ]
[ 2407-11-6 ]
[ 1212-29-9 ]
[ 2387-23-7 ]
[ 4845-58-3 ]

Reference： [1] Journal of Organic Chemistry, 1937, vol. 2, p. 148,153

7
[ 81539-54-0 ]
[ 538-75-0 ]
[ 7270-63-5 ]
[ 2387-23-7 ]
[ 3621-71-4 ]

Reference： [1] Heterocycles, 1997, vol. 46, # 1, p. 503 - 508

8
[ 81539-54-0 ]
[ 538-75-0 ]
[ 7270-63-5 ]
[ 2387-23-7 ]
[ 70392-95-9 ]
[ 3621-71-4 ]

Reference： [1] Heterocycles, 1997, vol. 46, # 1, p. 503 - 508

9
[ 2387-23-7 ]
[ 2438-38-2 ]

Reference： [1] Patent: US4117004, 1978, A,

10
[ 98446-49-2 ]
[ 372-09-8 ]
[ 538-75-0 ]
[ 846023-24-3 ]
[ 2387-23-7 ]

Reference： [1] Patent: US2005/43537, 2005, A1, . Location in patent: Page/Page column 6

[ 2387-23-7 ] Synthesis Path-Downstream 1~90

1
[ 64-17-5 ]
[ 2407-11-6 ]
[ 1212-29-9 ]
[ 2387-23-7 ]
[ 4845-58-3 ]

Reference： [1]Journal of Organic Chemistry,1937,vol. 2,p. 148,153

2
[ 108-91-8 ]
[ 57-13-6 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogenchloride In 5,5-dimethyl-1,3-cyclohexadiene at 120 - 130℃; for 12h; Inert atmosphere;	1.1; 2.1; 3.1 1. Substitution reaction step: a 500mL four-necked round-bottomed flask is placed in an electromagnetic stirrer heated by an oil bath, equipped with a spherical condenser, a thermometer, and a nitrogen gas inlet pipe. The outlet of the spherical condenser is connected to a buffer bottle and a 10% hydrochloric acid absorption bottle. , 60g urea,185g of cyclohexylamine and 312g of xylene were added to the reaction flask, start stirring, slowly heat up to reflux, the temperature is about 120-130°C,Ammonia gas is slowly released during the reflux process. The ammonia gas is collected and compressed for storage. At the same time, there is solid precipitation, and the reaction is stirred for 12 hours. After no ammonia gas is released, stop heating, remove the heater, and slowly cool down to below 30 °C. condenser, thermometer,The solid-liquid reaction was filtered to obtain 235g of solid dicyclohexylurea (DCU), the weight after drying was 205g, and the yield was 98%;
96%	With anhydrous zinc chloride at 80 - 85℃; for 0.166667h; Neat (no solvent);
95%	With iodine at 90 - 95℃; for 0.166667h;

95%	With graphene oxide In neat (no solvent) at 80℃; for 4h; Sealed tube;
89%	With sulfated polyborate at 120℃; for 2h;	General procedure for the synthesis of (un)symmetrical 1,3-disubstituted ureas and 1H-benzimidazol-2(3H)-ones General procedure: A mixture of amine (4 mmol or 2 mmol), or substituted OPDA (2 mmol), urea (2.4mmol), or N-phenylurea (2 mmol) and sulfated polyborate (10 wt%) was heated at 120°C in an oil bath. The reaction was monitored by thin layer chromatography. After completion of the reaction, the mixture was cooled to room temperature and quenched by water (5 mL); solid precipitated was filtered at vacuum pump, washed with water (3×5 mL), dried under vacuum and recrystallized from ethanol to afford the pure product.
	With i-Amyl alcohol
79 %Chromat.	With C₃₀H₃₀N₆O₂⁽²⁺⁾*2ClO₄^(1-) In neat (no solvent) at 120℃; for 20h; Inert atmosphere; Green chemistry;	2.4. Typical transamidation procedure General procedure: The amide (5.0 mmol), amine (5.5 mmol), and dicationic IL cat-alyst DAFBimIL-3d (1.0 mmol) were loaded in a 50 mL RB flask and the mixture was stirred at required temperature for particular time under nitrogen atmosphere. Progress of the reactions was monitored by TLC. After completion of the reaction, the transamide products were extracted in ethyl acetate (3 × 15 mL) and filtered to recover the catalyst. Ethyl acetate was removed using rotary evaporator and the obtained crude transamide products were purified using column chromatography and characterized by NMR and Mass spectrometry. Finally, the filtered solid IL catalysts were washed thoroughly with ethyl acetate, dried in vacuum at 60C for 2 h and then reused for the next run. All the transamidation reactions have been carried out at least three times to ensure the reproducibility of our results and the precision of our yields are presented in the respective tables.

Reference： [1]Current Patent Assignee: HUBEI CHUWEI PHARMACEUTICAL CO LTD - CN114149346, 2022, A Location in patent: Paragraph 0011; 0013-0015
[2]Location in patent: experimental part Pasha; Madhusudana Reddy [Synthetic Communications, 2009, vol. 39, # 16, p. 2928 - 2934]
[3]Pasha; Jayashankara [Synthetic Communications, 2006, vol. 36, # 12, p. 1787 - 1793]
[4]Patel, Khushbu P.; Gayakwad, Eknath M.; Patil, Vilas V.; Shankarling, Ganapati S. [Advanced Synthesis and Catalysis, 2019, vol. 361, # 9, p. 2107 - 2116]
[5]Rekunge, Deelip S.; Khatri, Chetan K.; Chaturbhuj, Ganesh U. [Tetrahedron Letters, 2017, vol. 58, # 45, p. 4304 - 4307]
[6]Amiard; Heymes [Bulletin de la Societe Chimique de France, 1956, p. 1360]
[7]Muskawar, Prashant Narayan; Thenmozhi; Bhagat, Pundlik Rambhau [Applied Catalysis A: General, 2015, vol. 493, p. 158 - 167]

3
[ 2387-23-7 ]
[ 538-75-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With dichloromethylenedimethyliminium chloride; triethylamine In dichloromethane at 0℃;
99.5%	With bis(trichloromethyl) carbonate In 1-methyl-pyrrolidin-2-one at 30 - 40℃; for 6h; Autoclave;	3 Example 1 1000 ml of NMP and 100 g of DCU were added to the autoclave at 30 ° C, stirred well, 200 g of BTC was added, and thenAdding the composite catalyst (the dosage ratio of DCU and composite catalyst is 1: 0.0001), raising the temperature to 40 DEG C,Reaction 6h, after the completion of the reaction, add triethylamine to adjust the pH to 7.5, hot filter, atmospheric distillation of the solvent, and then vacuum distillationDistillate, collecting 155 ± 1 ° C distillate, in the oven vacuum drying to obtain a white crystalline solid DCC.
97.3%	With pyridine; chloroacetyl chloride In dichloromethane at 0 - 60℃; for 10h;	1-6 Example 5 Put 50g DCU into a dry 500mL three-neck bottle, 300 mL of dichloromethane, 0.1g pyridine, Stir well, 37.8 g of chloroacetyl chloride was dissolved in 100 mL of dichloromethane and added dropwise to a three-neck bottle. The control addition time is 5h, the dropping temperature is 0±2°C, and after the addition is completed, the temperature is raised to 60°C, and the stirring reaction is carried out for 5 hours. After the reaction is completed, ammonia gas is introduced to adjust the pH to neutral. Then suction filtration, the filtrate is often distilled by distillation to remove the solvent. Then distilled under reduced pressure at a pressure of 1.35 - 1.54 KPa. The 153-156 ° C fraction was collected and dried under vacuum to obtain a product with a purity of 99.1%. The yield was 97.3%.

93.7%	With oxygen In hexane at 120℃; for 2.5h; Autoclave;	1 Adding N,N'-bicyclohexyl thiourea to the autoclave,Using n-hexane as a solvent,The mass ratio of N,N'-dicyclohexylurea to n-hexane solvent is 1.9:1,Adding V2O5-P2O5 catalyst,The amount of V2O5-P2O5 catalyst is 2% of the total amount of materials.Passing oxygen,The mass ratio of N,N'-dicyclohexylurea to oxygen is 1:0.15,Warming up to 10 MPa pressure toOxidation reaction at 120 ° C for 2.5 h,Then cool down to 15 ° C, suction filtration, decolorization,Distillation under reduced pressure gave DCC.The yield is 93.7%.Purity is 99.28%,The waste water produced by oxidation can be recycled after being tested by distillation.
92.54%	With bis(trichloromethyl) carbonate; ethyl acetoacetate at 10 - 50℃; for 4h; Molecular sieve;	1; 2; 3; 4; 5; 6; 7; 8; 9 Example 3 Stir and cool 200g of dicyclohexylurea (DCU) and 1000g of ethyl acetoacetate at room temperature to about 10°C.Add 420g of ditrichloromethyl carbonate, 2.1g of tin tetrachloride loaded on molecular sieve, heat up to 50, keep refluxing for 4h,Cool down to 5, add diethylene triamine dropwise, adjust the pH to 8-9,The reaction solution was filtered, the solvent was distilled off, and the product N,N'-dicyclohexylcarbodiimide was obtained by distillation under reduced pressure at 0.9-1.2KPa, with a yield of 92.54% and a purity of 99.28%.
91.7%	Stage #1: 1,3-Dicyclohexylurea With oxalyl dichloride In tert-butyl methyl ether at 25 - 35℃; for 3.5h; Stage #2: With sodium hydroxide at 40 - 45℃; for 6h;	1-3 Example 1 Add 100g of dicyclohexylurea to a mixed system consisting of 200mL water and 200mL methyl tert-butyl ether and stir for 30min,After suction filtration, it is placed in a vacuum oven and dried at 50 to constant weight.Put 50 g of dicyclohexylurea and 300 mL of methyl tert-butyl ether in a dry three-necked bottle, and stir well. At 25-35 , add 42.5g of oxalyl chloride to the three-necked bottle,Control the dropping time to 3 hours, The drop temperature is,Keep warm for 0.5h after the addition. Take 26.8g of sodium hydroxide and make up 15% alkali.At 40-45 , the reaction was added dropwise to the alkali, the drop time was controlled to 6h.Then it is filtered by suction, and the organic phase is obtained after the filtrate is separated into layers.Frequent pressure distillation to remove the solvent,Then distill under reduced pressure under the pressure of 1.35-1.54KPa, collecting 153-156 ° C fractions,The product was obtained after vacuum drying, with a purity of 99.6% and a yield of 91.7%.
91.39%	Stage #1: 1,3-Dicyclohexylurea With benzoyl chloride In N,N-dimethyl-formamide at 10 - 50℃; for 2.5h; Microwave irradiation; Stage #2: With trimethyldodecylammonium chloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 0.333333h; Microwave irradiation;	1-6; 1-3 Example 6 Using a microwave reactor, add 100g N,N'-dicyclohexylurea (DCU) to 400gN,N-dimethylformamide under a microwave radiation power of 180W at room temperature, and then cool to 10-12°C and add benzyl 240g acid chloride, 2.1g anhydrous tin tetrachloride supported on molecular sieve, heat up to 50, keep refluxing for 2.5h, and cool down to 5; add 0.9g phase transfer catalyst dodecyltrimethylammonium chloride, then drop Add triethylamine to adjust the pH value to 8-10, the alkali hydrolysis reaction occurs, the alkali hydrolysis reaction temperature is controlled to 20 , the alkali hydrolysis reaction time is 20 min, and the stirring speed of the alkali hydrolysis reaction is 300 revolutions/min; the reaction solution is filtered and separated Distillate the solvent, distill under reduced pressure at 0.9-1.1KPa, collect fractions at 135-145°C to obtain 84.17g of N,N'-dicyclohexylcarbodiimide, with a yield of 91.39% and a purity of 99.86%.
90%	With triphenylphosphine dibromide 1:1 addition complex; triethylamine In dichloromethane at 0℃; for 60h;
90%	With bromotriphenylphosphonium bromide; triethylamine In dichloromethane at 0℃; for 1h;
88%	With benzenesulfonyl chloride In dichloromethane at 40℃; for 3h;	1.2.3 2.3 Recovery of dicyclohexylurea: Dicyclohexylurea (448.5, 2.0 mol) was added to dichloromethane (1600 ml).Maintain 40 ° C ± 2 ° C, slowly add 430 g of benzenesulfonyl chloride, drop, continue to stir for 3 h,Cool to 0-5 ° C, slowly add 5% sodium hydroxide solution,Adjust pH=7, separate the organic layer, wash twice with water (800ml).Drying anhydrous sodium sulfate for 5 h, filtering, and distilling off the dichloromethane to recover dichloromethane.Switch to vacuum distillation and collect 155 ° C - 159 ° C / mmHg fraction,DCC (216.5 g, yield 88.0%) was obtained.
85.1%	With 3-Methyl-1-phenyl-2-phospholene 1-oxide at 140℃; for 18h;	1-3 Example 3: The by-product DCU (170 g) was placed in a 1000 mL reactor, and the catalyst 1-phenyl-3-ethyl-phospholene-1-oxide (2.1 g) was recovered and heated to 140 ° C for reaction.The reaction was carried out at about 140 ° C for 18 h, cooled to 60 ° C, and the catalyst was recovered by filtration. The filtrate was distilled under reduced pressure, and a fraction of 135-140 ° C (8 mmHg) was collected and cooled to give a white solid DCC.The yield was 85.1% and the purity was 98.4%.
82%	With trichlorophosphate In chloroform; water at 55 - 60℃; for 2h;	1 Example 1 The 5 kg N,N'-dicyclohexylurea raw material was placed in 10 kg of water and stirred for 40 min. The DCU was centrifuged and then dried in an oven at 110-120 ° C until the water was less than 0.5% 175 g of trichloromethane was added to a three-necked flask, and 40.0 g of dried DCU was added with stirring. Weigh 30g of phosphorus oxychloride and add to a 250 mL dropping funnel. Stirring to the three-necked flask drop of phosphorus oxychloride, 30min added. After the addition, the reaction is maintained between 55-60 ° C for 2 hours. The reaction solution was poured into a dropping funnel. The reaction was filtered while hot, and the solid component was washed twice with 20 g of trichloromethane. The filtrate was allowed to stand for 1.5 hours and divided into an organic layer and an aqueous layer containing phosphate and sodium chloride. The water layer and the intermediate layer are filtered. The filtrate is allowed to stand for more than 12 hours. Take the supernatant as the water for the configuration of the lye. The solid components were washed twice with 20 g of trichloromethane and the organic layers of the washings were combined and the chloroform was separated by distillation. The components were collected by distillation under reduced pressure at 122-124 ° C / 6 mmHg to obtain a DCC product, As a raw material solvent reuse. 30 g of DCC was obtained in a yield of 82%, and the purity of DCC as determined by gas chromatography was 99.5%
78%	With 1,2-dibromo-1,1,2,2-tetrachloroethane; triethylamine; triphenylphosphine In 1,2-dichloro-ethane at 0℃; for 0.0166667h;
78%	With iodine; triethylamine; triphenylphosphine In dichloromethane for 1h; Sonication;	General procedure for the synthesis of carbodiimide General procedure: To a solution of 0.0844 g iodine (0.33 mmol) and 0.0872 g triphenylphosphine (0.33 mmol) in 2 cm3 CH2-Cl2 was added a solution of thiourea or urea(0.275 mmol) and 0.0701 g triethylamine (0.69 mmol) in2 cm3 CH2Cl2 under sonication. The reaction mixture was further sonicated until completion of the reaction as indicated by TLC. The crude mixture was concentrated under reduced pressure then purified by column chromatography using hexane to give the carbodiimide (see supporting information for characterization data of all products).
10%	With dichlorocarbene
	With sodium hydroxide; sodium hypochlorite; Petroleum ether
	With sodium chlorite; dichloromethane
	With bromine; triethylamine; triphenylphosphine In dichloromethane at 0℃; for 30h;
	With potassium carbonate; 4-bromobenzenesulfonyl chloride In chloroform for 8h; Heating; Yield given;
	With dicarbonyl(cyclopentadienyl)methyliron(II); Triethoxysilane In tetrahydrofuran at 60℃; for 24h; Schlenk technique; Inert atmosphere;
74 %Chromat.	With (dimethoxy)methylsilane; copper diacetate; 1,2-bis-(dicyclohexylphosphino)ethane In tetrahydrofuran at 70℃; for 24h; Sealed tube;
	Multi-step reaction with 2 steps 1: trichlorophosphate / tetrahydrofuran / 50 °C 2: triethylamine / tetrahydrofuran
	With basic lead(II) carbonate; benzene
	With dichloromethane; alkaline aqueous NaBrO

Reference： [1]Schlama; Gouverneur; Mioskowski [Tetrahedron Letters, 1996, vol. 37, # 39, p. 7047 - 7048]
[2]Current Patent Assignee: XINJIANG KANGRUNJIE ENVIRONMENT PROTECTION SCIENCE AND TECHNOLOGY CO LTD - CN105503656, 2016, A Location in patent: Paragraph 0027; 0028
[3]Current Patent Assignee: SHANDONG JINCHENG COURAGE CHEMICAL - CN109232319, 2019, A Location in patent: Paragraph 0021-0032
[4]Current Patent Assignee: SHANDONG JINCHENG PHARMACEUTICAL & CHEMICAL CO., LTD. - CN109485584, 2019, A Location in patent: Paragraph 0018; 0019; 0020; 0021; 0022; 0023; 0024; 0025
[5]Current Patent Assignee: SHANDONG JINCHENG COURAGE CHEMICAL - CN112759534, 2021, A Location in patent: Paragraph 0013; 0027-0045
[6]Current Patent Assignee: SHANDONG JINCHENG COURAGE CHEMICAL - CN110903218, 2020, A Location in patent: Paragraph 0018-0023
[7]Current Patent Assignee: SHANDONG JINCHENG COURAGE CHEMICAL - CN112661669, 2021, A Location in patent: Paragraph 0032-0051
[8]Palomo, Claudio; Mestres, Ramon [Synthesis, 1981, # 5, p. 373 - 374]
[9]Palomo, Claudio; Mestres, Ramon [Bulletin de la Societe Chimique de France, 1981, vol. <II> 2, # 9-10, p. 361 - 364]
[10]Current Patent Assignee: HUNAN INST FOR DRUG CONTROL HUNAN PHARMACEUTICAL E - CN108424383, 2018, A Location in patent: Paragraph 0022; 0030; 0031
[11]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN109081792, 2018, A Location in patent: Paragraph 0011; 0022-0029
[12]Current Patent Assignee: SHANDONG JUYE FINE CHEMICAL - CN104262200, 2016, B Location in patent: Paragraph 0038-0043
[13]Bringmann, Gerhard; Schneider, Stephan [Synthesis, 1983, # 2, p. 139 - 141]
[14]Duangkamol, Chuthamat; Pattarawarapan, Mookda; Phakhodee, Wong [Monatshefte fur Chemie, 2016, vol. 147, # 11, p. 1945 - 1949]
[15]Schroth, Werner; Kluge, Helmut; Matthias, Michael; Krieg, Reimar; Schaedler, Hans-Dieter [Zeitschrift fur Chemie, 1981, vol. 21, # 1, p. 25 - 27]
[16]Lowenstein [Biochemical Journal, 1957, vol. 65, p. 197,199][Biochemical Preparations, 1960, vol. 7, p. 5,11] Schmidt; Seefelder [Justus Liebigs Annalen der Chemie, 1951, vol. 571, p. 83,85]
[17]Schmidt et al. [Justus Liebigs Annalen der Chemie, 1958, vol. 612, p. 11,17]
[18]Mestres, Ramon; Palomo, Claudio [Synthesis, 1980, # 9, p. 755 - 757]
[19]Jaszay, Zsuzsa M.; Petnehazy, Imre; Toeke, Laszlo; Szajani, Bela [Synthesis, 1987, # 5, p. 520 - 523]
[20]Hayasaka, Kazumasa; Fukumoto, Kozo; Nakazawa, Hiroshi [Dalton Transactions, 2013, vol. 42, # 28, p. 10271 - 10276]
[21]Liu, Richard Y.; Bae, Minwoo; Buchwald, Stephen L. [Journal of the American Chemical Society, 2018, vol. 140, # 5, p. 1627 - 1631]
[22]O'Brien, Alexander G.; Ricci, Eric M.; Journet, Michel [Organic Process Research and Development, 2018, vol. 22, # 3, p. 399 - 402]
[23]Current Patent Assignee: PFIZER INC - US2479498, 1946, A
[24]Current Patent Assignee: BAYER AG - DE823445, 1951, C [DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.]

4
[ 2387-23-7 ]
[ 17969-20-9 ]
[ 40361-65-7 ]

Reference： [1]Journal of medicinal chemistry,1972,vol. 15,p. 1040 - 1045

5
[ 2387-23-7 ]
[ 114316-64-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With oxalyl dichloride; toluene-4-sulfonic acid In 1,2-dimethoxyethane at 0 - 10℃; for 4h; Inert atmosphere;	1.2; 2.2; 3.2 2. Chlorine deamination step: 500mL four-necked round bottom flask,Equipped with spherical condenser, constant pressure dropping funnel and thermometer, put it into the electromagnetic stirrer of ethylene glycol water cooling bath, after nitrogen replacement three times, add 72g DCU, 0.06g p-toluenesulfonyl chloride and 200g ethylene glycol dimethyl ether, At 0°C under stirring, 25g of oxalyl chloride was slowly added dropwise for 1h. After the dropwise addition was completed, the stirring was continued at 10°C for 3h, then the dropping funnel was removed and an ammonia gas insertion tube was installed. , the outlet of the condenser is connected to the buffer bottle and the 10% hydrochloric acid absorption bottle, and then the ammonia gas collected in the first step is slowly passed through the flow meter, and the ammonia gas is passed through for 4.5 hours, and the flow rate is controlled at 60 mL/min. 11g, control pH=8, then introduce nitrogen for 30min, drive out the ammonia gas in the reaction flask, cool down to 0°C, stir for 1h to stop stirring, filter the solid-liquid mixture in the reaction flask to obtain about 30g of solid ammonium chloride, Content is 98.5%, obtains filtrate 260g, DCC chromatographic analysis, its reaction yield reaches 98%;
	With 1,2-dichloro-ethane
	With COCl₂ In benzene

With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 30℃; for 5.5h;

1-4 Example 2 Add 4.5g DMF to 52g SOCl2 and stir for 30min for later use. Put 50g of DCU and 300mL of dichloromethane into a dry 500mL three-necked flask and stir evenly. Add the prepared SOCl2/DMF solution dropwise to the three-necked flask, control the dropping time to 0.5h, and the dropping temperature to 30. After the dropping, continue to stir and react for 5h. After the reaction, the reaction liquid was added dropwise to 530g of NaOH aqueous solution with a mass concentration of 10%, and then filtered with suction. The filtrate was distilled under normal pressure to remove the solvent, and then distilled under reduced pressure at a pressure of 1.35-1.54KPa to collect fractions at 153-156°C. After drying, the product was obtained with a purity of 98.9% and a yield of 92.4%.

Reference： [1]Current Patent Assignee: HUBEI CHUWEI PHARMACEUTICAL CO LTD - CN114149346, 2022, A Location in patent: Paragraph 0011; 0013-0015
[2]Ulrich,H. et al. [Journal of Organic Chemistry, 1964, vol. 29, p. 2401 - 2404]
[3]Ulrich,H.; Sayigh,A.A.R. [Angewandte Chemie, 1966, vol. 78, p. 761 - 769]
[4]Current Patent Assignee: SHANDONG JINCHENG COURAGE CHEMICAL - CN112079748, 2020, A Location in patent: Paragraph 0021-0029

6
[ 201230-82-2 ]
[ 108-91-8 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: carbon monoxide; cyclohexylamine With selenium at 20℃; for 2h; neat (no solvent); Stage #2: With oxygen at 20℃; for 1h; neat (no solvent);
99%	With palladium; oxygen; potassium iodide In 1,4-dioxane at 130℃; for 24h; Autoclave; Green chemistry;
96%	With oxygen In tetrahydrofuran at 90℃; for 72h; Autoclave; Schlenk technique; Inert atmosphere;

94%	With hydrogenchloride; di-tert-butyl peroxide; montmorillonitebipyridinepalladium(II)acetate; copper dichloride In methanol for 10h; Ambient temperature;
90%	Stage #1: carbon monoxide; cyclohexylamine With sulfur at 80℃; for 4h; Stage #2: With oxygen at 20℃; for 1h; Further stages.;
88.3%	With oxygen In methanol at 80℃; for 6h;
84%	With salcomine; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; oxygen In toluene at 170℃; for 7h; Autoclave;	Representative reaction procedure: 10 mmol of substrate, 0.05 mmol of Cosalen, 0.03 mmol TBD, 20 ml of toluene were put in a glass liner, fitted in an autoclave, charged with oxygen (2 bar) and carbon monoxide (22 bar) and heated in a thermoregulated oil bath at 140 °C for 7 h. The autoclave was then allowed to cool to room temperature and degassed. Direct recovery of the ureas from the reaction medium was obtained by cooling the reaction mixture to 0 °C. The resulting precipitate was filtered and re-crystallized from methanol. The other products were recovered after evaporation of the solvent under reduced pressure and silica gel chromatography (Merck 0.05-0.2 mm (R = 50), using dichloromethane-ethyl acetate 1:1 as the eluting mixture. Isolated products were characterized by MS, IR, and 1H NMR and the related spectra were compared with the literature data.
76%	With copper diacetate; air In toluene for 2h; Heating;
60%	With oxygen; potassium iodide In neat (no solvent) at 122℃; for 6h; Green chemistry;
57%	With iodine; potassium carbonate In acetonitrile at 95℃; for 3h;
37%	With 2C₇H₉N₄Au⁽¹⁺⁾Cu⁽¹⁺⁾*2I^(1-) In toluene at 60℃; for 40h; Autoclave;
19%	With oxygen In 1,4-dioxane at 100℃; for 3h;
	With selenium; 3-trifluoromethylnitrobenzene In chlorobenzene at 80℃;
	With [Pd(phen)Cl₂]; oxygen; 1-butyl-3-methylimidazoliumhydroxide In methanol at 175℃; for 1h;
71 % Chromat.	With tetrabutylammonium tetrafluoroborate; sodium acetate In acetonitrile at 50℃; for 6h; Electrolysis;
	With sulfur; sodium nitrite In methanol at 120℃; for 10h;
69 %Chromat.	With C₆₆H₁₀₅Au₃N₃⁽¹⁺⁾*BF₄^(1-); oxygen In tetrahydrofuran at 90℃; for 45h;
49 %Chromat.	With oxygen; copper dichloride In water at 100℃; for 4h; Autoclave; Green chemistry;	Materials and general procedure General procedure: In a typical experiment the glass vial was charged with a dou-bled distilled water solution (5.0 mL) of substrate (amine or aminol) (4 mmol), catalyst (CuCl2, 0.40 mmol), which appeared transparentand deep blue colored. The vial was introduced into the autoclave which was sealed, purged and charged with O2(0.6 MPa) and CO upto a total pressure of 4 MPa. Under these conditions, the substrate should be deemed the limiting reagent, also taking into account the head space of the autoclave and the stoichiometry of the carbony-lation process [Eq. (1)].The mixture was heated at 100C and allowed to react for 4 h.After this time, the autoclave was cooled at room temperature and then the residual gas was evacuated Identification of reaction products was performed via GC-MS bycomparison of their MS spectra with those reported in the litera-ture (and with the help of NIST database). A complete list of massspectral data of the major reaction products, including by-products,was reported into the supplementary material section. Quantitativeanalysis of reaction mixture was accomplished by GC-MS usingbutanone as an external standard. Conversions and yields were reported in Tables 1-3.
55 mg	With C₆₂H₅₂AgAu₄N₂O₄P₄⁽³⁺⁾*3F₆Sb^(1-) In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Mizuno, Takumi; Nakai, Takeo; Mihara, Masatoshi [Synthesis, 2010, # 24, p. 4251 - 4255]
[2]Liu, Shujuan; Wang, Hongli; Dai, Xingchao; Shi, Feng [Green Chemistry, 2018, vol. 20, # 15, p. 3457 - 3462]
[3]Duan, Hui; Zeng, Yongfei; Yao, Xin; Xing, Pengyao; Liu, Jia; Zhao, Yanli [Chemistry of Materials, 2017, vol. 29, # 8, p. 3671 - 3677]
[4]Choudary; Koteswara Rao [Synthetic Communications, 1991, vol. 21, # 18-19, p. 1923 - 1927]
[5]Mizuno, Takumi; Mihara, Masatoshi; Nakai, Takeo; Iwai, Toshiyuki; Ito, Takatoshi [Synthesis, 2007, # 20, p. 3135 - 3140]
[6]Giannoccaro, Potenzo [Journal of Organometallic Chemistry, 1987, vol. 336, p. 271 - 278]
[7]Location in patent: experimental part Saliu, Francesco; Putomatti, Benedetto; Rindone, Bruno [Tetrahedron Letters, 2012, vol. 53, # 28, p. 3590 - 3593]
[8]Orito, Kazuhiko; Miyazawa, Mamoru; Nakamura, Takatoshi; Horibata, Akiyoshi; Ushito, Harumi; Nagasaki, Hideo; Yuguchi, Motoki; Yamashita, Satoshi; Yamazaki, Tetsuro; Tokuda, Masao [Journal of Organic Chemistry, 2006, vol. 71, # 16, p. 5951 - 5958]
[9]Liu, Shujuan; Dai, Xingchao; Wang, Hongli; Shi, Feng [Green Chemistry, 2019, vol. 21, # 15, p. 4040 - 4045]
[10]Pri-Bar, Ilan; Alper, Howard [Canadian Journal of Chemistry, 1990, vol. 68, # 9, p. 1544 - 1547]
[11]Cao, Yanwei; Yang, Jian-Gong; Deng, Yi; Wang, Shengchun; Liu, Qi; Shen, Chaoren; Lu, Wei; Che, Chi-Ming; Chen, Yong; He, Lin [Angewandte Chemie - International Edition, 2020, vol. 59, # 5, p. 2080 - 2084][Angew. Chem., 2020, vol. 132, # 5, p. 2096 - 2100,5]
[12]Zheng, Shuzhan; Li, Fuwei; Liu, Jianming; Xia, Chungu [Tetrahedron Letters, 2007, vol. 48, # 33, p. 5883 - 5886]
[13]Manov-Yuvenskii, V. I. [Russian Journal of Physical Chemistry, 1994, vol. 68, # 8, p. 1380 - 1382][Zhurnal Fizicheskoi Khimii, 1994, vol. 68, # 8, p. 1520 - 1522]
[14]Shi, Feng; Peng, Jiajian; Deng, Youquan [Journal of Catalysis, 2003, vol. 219, # 2, p. 372 - 375]
[15]Chiarotto, Isabella; Feroci, Marta [Journal of Organic Chemistry, 2003, vol. 68, # 18, p. 7137 - 7139]
[16]Peng, Xingao; Li, Fuwei; Xia, Chungu [Synlett, 2006, # 8, p. 1161 - 1164]
[17]Jin, Liqun; Weinberger, David S.; Melaimi, Mohand; Moore, Curtis E.; Rheingold, Arnold L.; Bertrand, Guy [Angewandte Chemie - International Edition, 2014, vol. 53, # 34, p. 9059 - 9063][Angew. Chem., 2014, vol. 126, # 34, p. 9205 - 9209,5]
[18]Casiello, Michele; Iannone, Francesco; Cotugno, Pietro; Monopoli, Antonio; Cioffi, Nicola; Ciminale, Francesco; Trzeciak, Anna M.; Nacci, Angelo [Journal of Molecular Catalysis A: Chemical, 2015, vol. 407, p. 8 - 14]
[19]Smirnova, Ekaterina S.; Muñoz Molina, José M.; Johnson, Alice; Bandeira, Nuno A. G.; Bo, Carles; Echavarren, Antonio M. [Angewandte Chemie - International Edition, 2016, vol. 55, # 26, p. 7487 - 7491][Angew. Chem., 2016, vol. 128, # 26, p. 7613 - 7617]

7
[ 3173-53-3 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With [Pr(SPh)3(THF)3] In tetrahydrofuran at 60℃; for 12h; Inert atmosphere;	4.3. General procedure for the cyclotrimerization or cyclodimerization of isocyanates catalyzed by [Pr(SPh)₃(THF)₃] (2a as an example) General procedure: To a 30 mL Schlenk tube under dried argon were added [Pr(SPh)3(THF)3] (0.0137 g, 0.02 mmol), THF (10 mL), and phenyl isocyanate (0.216 mL, 2.00 mmol). When the resulting mixture was stirred at 60 °C for 12 h, it was hydrolyzed by water (1 mL), extracted with diethyl ether (3×10 mL), dried over anhydrous MgSO4, and filtered. After removal of the solvent from the extract under the reduced pressure, the solid was re-crystallized in THF and toluene and filtered off. The filtrate was allowed to stand at -18 °C for several days, forming colorless crystals of 1,3,5-trisphenyl-1,3,5-triazinane-2,4,6-trione (2a) in 97% yield.
92%	With Trimethylsilanol In acetonitrile at 20℃; Green chemistry;	General procedure for the synthesis of symmetrically substituted urea 3 General procedure: MeCN (10 mL, anhydrous) and then trimethylsilanol (2, 1.0 mmol) were added to a well-stirred isocyanate (1, 1.0 mmol). The reaction mixture was stirred for 3-6 h at room temperature. After that, the solvent was removed to afford the corresponding symmetrically substituted urea product 3.
89%	With Ta(η⁵-C5Me5)(η³-1-phenylallyl)2 In toluene for 12h; Ambient temperature;

85%	Stage #1: Cyclohexyl isocyanate With [nido-6-Mn(CO)₃B₉H₁₃][NMe₄] In dichloromethane for 0.166667h; Inert atmosphere; Sonication; Stage #2: In dichloromethane for 0.166667h; Irradiation; Inert atmosphere;	4.3.4 Cyclohexyl isocyanate with compound 1 Compound 1 (0.001g, 0.003mmol) and 0.019g (0.15mmol) of Cyclohexyl isocyanate in 5mL dichloromethane were placed in a 10mL flask and sonicated for 10min before being put in the photoreactor for 10min. It was then hydrolyzed by 1mL water, extracted with diethyl ether (3×10mL), dried over anhydrous MgSO4, and filtered. After removal of the solvent from the extract, the solid was re-crystalized in THF and filtered off. It gave 0.016g (85%) colorless crystal of 1,3-dicyclohexylurea. 1H NMR (300 MHz, CD2Cl2, δ δ (ppm)): 4.06 (2H, NH), 3.50-3.46 (2H, CH), 2.01-1.92 (4H, CH2), 1.71-1.61 (8H, CH2), 1.40-1.29 (4H, CH2), 1.16-1.04 (4H, CH2). 13C NMR(75.47 MHz, CD2Cl2, δ δ (ppm)): 157.3, 48.4, 34.7, 25.9, 25.0. MS: m/z=125.13.
68%	With C₂₄H₂₈N₈PrS₄^(1-)*Li⁽¹⁺⁾ In acetonitrile at 60℃; for 12h; Inert atmosphere;
	With water; tetraethylammonium fluoride In acetonitrile electrolysis; Yield given;

Reference： [1]Location in patent: experimental part Wang, He-Ming; Li, Hong-Xi; Yu, Xiang-Yang; Ren, Zhi-Gang; Lang, Jian-Ping [Tetrahedron, 2011, vol. 67, # 8, p. 1530 - 1535]
[2]Wu, Xingxing; Niu, Qingfen; Li, Tianduo [Synthetic Communications, 2016, vol. 46, # 16, p. 1364 - 1369]
[3]Mashima, Kazushi; Yamanaka, Yoshimichi; Gohro, Yoshihiko; Nakamura, Akira [Journal of Organometallic Chemistry, 1993, vol. 459, # 1-2, p. 131 - 138]
[4]Ma, Pei; Spencer, James T. [Polyhedron, 2018, vol. 149, p. 148 - 152]
[5]Location in patent: experimental part Li, Hong-Xi; Cheng, Mei-Ling; Wang, He-Ming; Yang, Xiao-Juan; Ren, Zhi-Gang; Lang, Jian-Ping [Organometallics, 2011, vol. 30, # 2, p. 208 - 214]
[6]Becker, James Y.; Zinger, Baruch; Yatziv, Shimon [Journal of Organic Chemistry, 1987, vol. 52, # 13, p. 2783 - 2789]

8
[ 2387-23-7 ]
[ 71-43-2 ]
[ 827-52-1 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 2913 - 2914

9
[ 1212-29-9 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogenchloride; sodium nitrite In dichloromethane; water at 20℃; for 0.25h;
96%	With sodium periodate for 1.33333h; Ambient temperature; further reagents;
95%	With potassium superoxide; 18-crown-6 ether In dimethyl sulfoxide for 36h; Ambient temperature;

82%	With benzenetellurinyl trifluoroacetate In dichloromethane for 12h; Ambient temperature;
81%	With tert-butylhypochlorite In tetrachloromethane; ethanol at 25℃; for 0.166667h;
86 % Chromat.	With hydrogenchloride; N-nitrosopiperidine; potassium iodide In dichloromethane; water at 22℃; for 48h;
	With mercury(II) diacetate; formic acid hydrazide In N,N-dimethyl-formamide; acetonitrile at 20℃; for 2h;
	With sodium hypochlorite In benzene	Synthesis of N, N'-dicyclohexylcarbodiimide: To the kettle was added xylene and the reaction of cyclohexylamine,Control the temperature drop of carbon disulfide, drop Bi warming,After removing the hydrogen sulfide,N, N'-dicyclohexylthiourea was obtained by filtration.N, N'-dicyclohexylthiourea was charged into a reaction vessel,Add benzene andcatalyst,Controlled temperature dropping sodium hypochlorite,Insulation after filtration water,The organic phase is subjected to distillation and rectification to give N, N'-dicyclohexylcarbodiimide.

Reference： [1]Joergensen, K. A.; Ghattas, A.-B.A.G.; Lawesson, S.-O. [Tetrahedron, 1982, vol. 38, # 9, p. 1163 - 1168]
[2]Ramadas; Janarthanan [Synthetic Communications, 1997, vol. 27, # 13, p. 2357 - 2362]
[3]KIM, Yong Hae; YON, Gyu Hwan; KIM, Hyung Jin [Chemistry Letters, 1984, p. 309 - 312]
[4]Fukumoto, Takahiro; Matsuki, Toshiaki; Hu, Nan Xing; Aso, Yoshio; Otsubo, Tetsuo; Ogura, Fumio [Chemistry Letters, 1990, # 12, p. 2269 - 2272]
[5]El-Wassimy, M.T.M.; Jorgensen, K.A.; Lawesson, S.-O. [Tetrahedron, 1983, vol. 39, # 10, p. 1729 - 1734]
[6]Jorgensen, K. A.; El-Wassimy, M. T. M.; Lawesson, S. -O. [Tetrahedron, 1983, vol. 39, # 3, p. 469 - 474]
[7]Natarajan, Amarnath; Guo, Yuhong; Arthanari, Haribabu; Wagner, Gerhard; Halperin, Jose A.; Chorev, Michael [Journal of Organic Chemistry, 2005, vol. 70, # 16, p. 6362 - 6368]
[8]Current Patent Assignee: SHANDONG JINCHENG PHARMACEUTICAL & CHEMICAL CO., LTD. - CN105439870, 2016, A Location in patent: Paragraph 0027

10
[ 538-75-0 ]
[ 1124-53-4 ]
[ 108-94-1 ]
[ 3173-53-3 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 16 % Chromat. 2: 90 % Chromat. 3: 4 % Chromat. 4: 52 % Chromat.	With lithium perchlorate In acetonitrile anodic oxidation;

Reference： [1]Becker, James Y.; Zinger, Baruch [Journal of the American Chemical Society, 1982, vol. 104, # 8, p. 2327 - 2329]

11
[ 2491-15-8 ]
[ 2387-23-7 ]
[ 101426-90-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1961,vol. 34,p. 4 - 6

12
[ 931-53-3 ]
[ 108-91-8 ]
[ 2387-23-7 ]
[ 538-75-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 35% 2: 10 % Chromat.	With oxygen; sodium carbonate In acetonitrile at 100℃; for 3h;

Reference： [1]Pri-Bar, Ilan; Schwartz, Jeffrey [Chemical Communications, 1997, # 4, p. 347 - 348]

13
[ 124-38-9 ]
[ 108-91-8 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: cyclohexylamine With titanium(IV) tetrachloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: With pyridine In dichloromethane for 0.5h; Inert atmosphere; Stage #3: carbon dioxide Further stages;
98%	With cesium hydroxide monohydrate; 1-n-butyl-3-methylimidazolium chloride at 170℃; for 4h;
96%	Stage #1: cyclohexylamine With Carbon tetrachloride; triphenylphosphine In dichloromethane for 24h; Heating; Stage #2: With triethylamine at 20℃; for 2h; Stage #3: carbon dioxide; cyclohexylamine at 20℃; for 24h; Further stages.;

85%	With Amberlite IRA-400; lithium hydroxide monohydrate; gold at 180℃; for 20h;
84.1%	With caesium hydroxide; 1-n-butyl-3-methylimidazolium chloride In 1-methyl-pyrrolidin-2-one at 170℃; for 4h;	1 Comparative example 1 CeO2 0.86g (5mmol) was placed in a reactor, and 20 ml of N-methylpyrrolidone, 2.48 g (25 mmol) of cyclohexylamine were charged to the reactor. The reactor was purged three times with carbon dioxide gas to remove residual air inside the reactor, the reactor was heated to 170 ° C and the carbon dioxide pressure was raised to 800 psig. After reacting at 170 ° C for 4 hours, the reaction mixture was cooled to room temperature, and the product was dissolved in methanol, and the product and the catalyst were separated using a vacuum filtration apparatus. GC and mass spectrometry analysis showed that the conversion of cyclohexylamine was 53%, the selectivity to 1,3-dicyclohexylurea was 84%, and the yield was 35.9%. In order to compare the heterogeneous catalyst used in the present invention with the homogeneous catalyst, 1,3-dicyclohexylurea was prepared by carrying out the reaction under the same conditions as in Example 3 except that the catalyst of the following Table 3 was used instead of the cerium oxide catalyst, the results are shown in Table 3.
81%	Stage #1: carbon dioxide; cyclohexylamine In dimethyl sulfoxide at 20℃; Stage #2: cyclohexylamine With triphenylphosphine; diethylazodicarboxylate In dimethyl sulfoxide at 20℃; for 2.5h; chemoselective reaction;
81%	With tris(acetylacetonato)cobalt(III); 1-n-butyl-2,3-dimethylimidazolium chloride at 160℃; for 10h; chemoselective reaction;
80%	With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC]iridium hexafluorophosphate; triphenylphosphine In acetonitrile at 20℃; for 12h; Schlenk technique; Sealed tube; Irradiation;
72%	With tetradecyltrihexylphosphonium imide at 60℃; for 8h;	1 Example 1 When [P66614] Im anionic functionalized ionic liquid absorption : ^ to achieve absorption equilibrium,According to : ^ saturated absorption,2 times the molar amount of cyclohexylamine was added to the ionic liquid system after absorbing C02,Mixed evenly transferred to the stainless steel high pressure reaction dad at 60 ° C and under atmospheric pressure in situ transformation reaction,After 8 hours of reaction, the reaction was stopped,Add a certain amount of distilled water,Separating the crude product and the ionic liquid,Recrystallization gave N, N'-dicyclohexylurea in a yield of 65%.
70%	With tetra-n-butylammonium tungstate In 1-methyl-pyrrolidin-2-one at 139.84℃; for 24h; Autoclave;
68%	With ferric(III) chloride; phenylsilane; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In tetrahydrofuran at 110℃; for 24h; Sealed tube;
65%	With cerium(IV) dioxide In 1-methyl-pyrrolidin-2-one at 129.84℃; for 24h; Autoclave;	2.2. Catalytic test General procedure: All the reactions were carried out in an autoclave reactor with aninner volume of 190 ml. The standard procedure of the 1,3-dibutylurea (DBU) synthesis from CO2 and n-butylamine was as follows:CeO2 (0.34 g, 2 mmol), n-butylamine 1.46 g (20 mmol) and Nmethylpyrrolidone(NMP) 8 ml (81 mmol) were put into the autoclavetogether with a spinner, and then the reactor was purged with1 MPa CO2 (Shimakyu Co., Ltd., >99.5%) three times. The autoclavewas pressurized with CO2 to the desired pressure (typically5.0 MPa) at room temperature, and then the autoclave was heatedto 433 K, where the CO2 pressure was about 12 MPa. In the experimentsfor determination of the reaction rates, the autoclave withsubstrate, solvent and catalyst was first purged with 1 MPa Ar(Taiyo Nippon Sanso Corporation >99.9999%) three times and pressuredwith Ar to 0.1 MPa. The autoclave was heated to 433 K andwas pressured with CO2 to 5.0 MPa (CO2 + Ar). The time when thetemperature reached 433 K was set as 0 h. The mixture was constantlystirred during the reaction. After the reaction time, the reactorwas cooled in water bath to room temperature. Methanol (10 ml) was added to the liquid phase as a solvent, and 1-hexanol(0.2 ml) was also added as an internal standard substance for aquantitative analysis. The reactor was washed with methanol, andthe liquids used in washing were added to the reaction mixture.The products were analyzed by a gas chromatograph equipped withan FID using a CP/Sil 5 CB capillary column (Agilent TechnologiesInc., length = 50 m, I.D. = 0.25 mm, df = 0.25 lm). The followingoperating conditions were used: carrier gas: N2, initial flow rate:0.86 ml/min (pressure control mode), split ratio: 55:1, injectiontemperature of 573 K, column temperature program: 313 K(7 min), 20 K/min to 433 K (4 min), 20 K/min to 473 K (10 min),and 20 K/min to 573 K (26 min), detection temperature of 573 K.The qualitative analysis of the products was conducted by a gaschromatograph equipped with a quadrupole mass spectrometer(GC-MS) using the same capillary column.
64.7%	at 180℃; for 24h; Autoclave;
48.9%	With potassium hydroxide at 149.84℃; for 10h; Autoclave;
28%	With Triethoxysilane; zinc powder In neat (no solvent) at 120℃; for 24h; Autoclave;
16%	With 2-pyrrolidinon at 170℃; for 4h; Autoclave;
16%	at 170℃; for 4h; Autoclave;	9; 17 Example 1 General procedure: Example 1To 100 mL of a high-pressure stainless steel reactor equipped with a thermocouple and electric heater, 100 mmol of ethylenediamine (Aldrich Chemical) and 20 mL of 2-pyrrolidone (Aldrich Chemical) as a solvent were added, followed by carbon dioxide (CO2). , Sin Yang Gas) was washed three times.The reactor was heated to 200° C. under a carbon dioxide pressure of 1.0 MPa. At 200° C. the carbon dioxide pressure was further increased to 5.0 MPa and maintained throughout the reaction through a carbon dioxide reservoir equipped with a high pressure regulator and pressure transducer. The reaction was carried out for 2 hours, after which the reactor was cooled to room temperature and then reduced pressure to prepare urea.
	Erhitzen des Reaktiosnsprodukts mit Al₂O₃ auf 200grad;
	With Mg-Al Layered Double Hydroxide calcined at 550°C In 1-methyl-pyrrolidin-2-one at 170℃; for 10h; Autoclave;
70 %Chromat.	With tetra-n-butylammonium tungstate In 1-methyl-pyrrolidin-2-one at 140℃; for 24h; Autoclave;	A typical procedure for the I-catalyzed reaction of aryldiamines General procedure: A typical procedure for the I-catalyzed reaction of aryl diamines with 1 atm CO2 was as follows: diamine (1 mmol), I (0.15 mmol), and N-methylpyrrolidone (NMP) (1 mL) were charged in a Schlenk tube with a magnetic stir bar. CO2 (1 atm) was introduced by a balloon, and the reaction mixture was stirred at 140 °C for 24 h. The reaction solution was periodically analyzed by GC, LC, GC-MS, or NMR. A Teflon vessel placed in a stainless steel autoclave was used for reactions with CO2 at 20 atm.
	In lithium hydroxide monohydrate at 180℃; for 5h;	7 Examination using various amines was also conducted under the same conditions as in Example 1, including examples comparing the presence or absence of an aqueous medium and the presence or absence of a carbonate. Table 1 shows the results of studies using various amines. From this, better yield was obtained when amines having longer chain alkyl chains were used as raw materials.
81 %Spectr.	With vanadium triisopropoxide oxide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 130℃; for 15h;
67.06 %Chromat.	at 160℃; for 4h; Autoclave;	2.3. Performance tests of catalysts General procedure: The catalytic performance test of alkali rich metal δ-MnO2 aimed at the carbonylation of amines with CO2 is carried out in a 50 mL stainless steel autoclave with Teflon lining, pressure gauge and magnetic stirring device with automatic constant temperature control function. In a typical run, firstly, 0.05 mol amine, 25 mL solventand 0.01 mol alkali rich metal δ-MnO2 are successively added to the autoclave, then, after the autoclave is tightly sealed, 5.0 MPa high-purity CO2 gas (purity > 99%) is continuously introduced for 20 min at room temperature, and then the CO2 inlet valve is closed. At the same time, the reaction temperature is slowly increased to the set value of 120 and the magnetic speed is 600 rpm, the reaction ends after 4 h, cools the autoclave to room temperature, opens it and filters the reaction mixture, the precipitate is washed to neutral with deionized water and placed in a constant temperature drying oven to dry at 80 for 24 h to obtain the recovered catalyst,The filtrate was analyzed qualitatively and quantitatively over agas chromatography mass spectrometry instrument (GC-MSQP2010 plus) equipped with a RXiTM-5MS capillary column(30 m 0.25 mm) and FID detector.. The conversion of raw organic amines and the selectivity of all products are calculated by external standard method the equation Wsp = WstAsp/Ast 100%, where spand st refer respectively to specimen and standard.

Reference： [1]Anderson, James C.; Moreno, Rafael Bou [Organic and Biomolecular Chemistry, 2012, vol. 10, # 7, p. 1334 - 1338]
[2]Shi, Feng; Deng, Youquan; SiMa, Tianlong; Peng, Jiajian; Gu, Yanlong; Qiao, Botao [Angewandte Chemie - International Edition, 2003, vol. 42, # 28, p. 3257 - 3260]
[3]Porwanski, Stanislaw; Menuel, Stephane; Marsura, Xavier; Marsura, Alain [Tetrahedron Letters, 2004, vol. 45, # 26, p. 5027 - 5029]
[4]Shi, Feng; Zhang, Qinghua; Ma, Yubo; He, Yude; Deng, Youquan [Journal of the American Chemical Society, 2005, vol. 127, # 12, p. 4182 - 4183]
[5]Current Patent Assignee: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGY - KR101540636, 2015, B1 Location in patent: Paragraph 0037; 0045-0047
[6]Location in patent: experimental part Chaturvedi, Devdutt; Mishra, Nisha; Mishra, Virendra [Monatshefte fur Chemie, 2008, vol. 139, # 3, p. 267 - 270]
[7]Location in patent: experimental part Li, Jian; Guo, Xiaoguang; Wang, Liguo; Ma, Xiangyuan; Zhang, Qinghua; Shi, Feng; Deng, Youquan [Science China Chemistry, 2010, vol. 53, # 7, p. 1534 - 1540]
[8]Zhang, Qian; Hou, Jing; Huang, Yan; Zhan, Le-Wu; Li, Bin-Dong [Chemical Communications, 2022, vol. 58, # 29, p. 4599 - 4602]
[9]Current Patent Assignee: SHAOXING UNIVERSITY - CN106008274, 2016, A Location in patent: Paragraph 0029-0030
[10]Kimura, Toshihiro; Kamata, Keigo; Mizuno, Noritaka [Angewandte Chemie - International Edition, 2012, vol. 51, # 27, p. 6700 - 6703]
[11]Zhao, Yulei; Guo, Xuqiang; Si, Zhiyao; Hu, Yanan; Sun, Ying; Liu, Yunlin; Ji, Zhongyin; You, Jinmao [Journal of Organic Chemistry, 2020, vol. 85, # 20, p. 13347 - 13353]
[12]Tamura, Masazumi; Ito, Kazuki; Nakagawa, Yoshinao; Tomishige, Keiichi [Journal of Catalysis, 2016, vol. 343, p. 75 - 85]
[13]Location in patent: experimental part Wu, Chaoyong; Cheng, Haiyang; Liu, Ruixia; Wang, Qiang; Hao, Yufen; Yu, Yancun; Zhao, Fengyu [Green Chemistry, 2010, vol. 12, # 10, p. 1811 - 1816]
[14]Kong, De-Lin; He, Liang-Nian; Wang, Jin-Quan [Synlett, 2010, # 8, p. 1276 - 1280]
[15]Du, Chongyang; Chen, Yaofeng [Chinese Journal of Chemistry, 2020, vol. 38, # 10, p. 1057 - 1064]
[16]Hwang, Junhyeok; Han, Donggu; Oh, Jin Joo; Cheong, Minserk; Koo, Hyun-Joo; Lee, Je Seung; Kim, Hoon Sik [Advanced Synthesis and Catalysis, 2019, vol. 361, # 2, p. 297 - 306]
[17]Current Patent Assignee: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGY - KR102157615, 2020, B1 Location in patent: Paragraph 0073-0075; 0134-0138; 0164-0165; 0168; 0196
[18]Hayashi; Kuyama [1951, vol. 2, p. 79,85][Chem.Abstr., 1954, p. 1274]
[19]Zhang, Ran; Hua, Li; Guo, Li; Song, Baoning; Chen, Jizhong; Hou, Zhenshan [Chinese Journal of Chemistry, 2013, vol. 31, # 3, p. 381 - 387]
[20]Kamata, Keigo; Kimura, Toshihiro; Sunaba, Hanako; Mizuno, Noritaka [Catalysis Today, 2014, vol. 226, p. 160 - 166]
[21]Current Patent Assignee: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY; UNITIKA LTD - JP5681985, 2015, B2 Location in patent: Paragraph 0050; 0051
[22]Moriuchi, Toshiyuki; Sakuramoto, Takashi; Matsutani, Takanari; Kawai, Ryota; Donaka, Yosuke; Tobisu, Mamoru; Hirao, Toshikazu [RSC Advances, 2021, vol. 11, # 44, p. 27121 - 27125]
[23]Fang, Yanxiong; Peng, Liang; Ping Jiang, San; Shao, Zongping; Sun, Dalei; Yang, Yating [Journal of Catalysis, 2022, vol. 409, p. 48 - 58]

14
[ 59178-92-6 ]
[ 765935-41-9 ]
17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester of 6-(2-methacryloylamino)hexanoic acid [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
46%	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at -18 - 4℃; for 18h;	1 17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-lH-cyclopenta[a]phenanthren-3-yl ester of 6-(2-methacryloylamino)hexanoic acid (MA-AH- chol) was prepared by reaction of methacrylated 6-aminohexanoic acid (prepared according to the previously described procedure [Ulbrich patents]) (MA-AH-OH) with cholesterol with use of the conjugating agent dicyclohexyl carbodiimide (DCC) in tetrahydrofuran (THF). 250 mg of MA-AH-OH (1.26 mmol) and 456 mg of cholesterol (1.26 mmol) was dissolved in freshly redistilled THF. 1.2 molar excess of DCC (311 mg, 1.51 mmol) was dissolved in 0.75 ml THF; the solution contained several crystals of λζN-dimethylaminopyridine (DMAP). Both solutions were cooled down to -18 °C. One hour after cooling, the solutions were poured together and the reaction mixture was left at -18 °C for 1 h and at 4 °C for 16 hours. Unreacted DCC was removed by reaction with 50 μl of concentrated acetic acid while stirred at room temperature, rn 0.5 hour the precipitated dicyclohexylurea (DCU) was removed by filtration, THF was evaporated and the product dissolved in ethyl acetate. Residues of precipitated DCU were again removed by filtration. Unreacted MA-AH-OH was removed by extraction with a 2 w. % NaHCO3 solution and MA-AH-chol was separated by crystallization from acetone and purified by recrystallization.Y=46 %, 329 mg. melting point: 93-95 °C, elementary analysis: theor. 78.25 % C, 10.83 % H, 2.47 % N, exp. 78.73 % C, 10.85 % H, 2.34 % N, TLC: ethyl acetate: hexane 1:1, Rf =0.8.

Reference： [1]Current Patent Assignee: ADVENT INTERNATIONAL CORPORATION - WO2007/110003, 2007, A2 Location in patent: Page/Page column 6

15
[ 325722-25-6 ]
[ 140-10-3 ]
[ 538-75-0 ]
(2S)-2-tert-butyloxycarbonylamino-1-trans-cinnamoylamino-3-methylbutane [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
88.7%	With benzotriazol-1-ol; triethylamine In tetrahydrofuran at 0 - 20℃;	2 Synthesis of(2S)-2-Tert-Butyloxycarbonylamino-l-trans-cinnamoylamino-3- methylbutane; The solution of (2S/)-l-amino-2-ter?-bytyloxycarbonylamino-3-methylbutane hydrochloride (2.38 g 10 mmol), triethylamine (1.7 ml, 12 mmol), HOBt(2.70 g. 20 mmol) and trαrø-cinnamic acid (1.77 g, 12 mmol) in 50 ml of tetrahydrofurane(THF) was cooled in an ice bath, and DCC (1.54g, 7.5 mmol) was added in small portions, during 30 min. The stirring was continued for 1 hour, and next the reaction mixture was left in room temperature overnight. The precipitate DCU was filtered off and washed with two portions of THF (15 ml of each). Combined filtrates were evaporated under reduced pressure and the solid residue was dissolved in 150 ml of ethyl acetate. The solution obtained was washed with ice-cold IM hydrochloric acid (3x50 ml), water (100 ml), a saturated water solution of sodium bicarbonate (3x 50 ml) and saline (2x50 ml). The organic layer was dried over anhydrous magnesium sulphate and evaporated to dryness. The resulting solid was crystallized from toluene - petroleum ether, yielding 2.95 g (88.7%) of (2S)-2- fert-butyloxvcarbonvlamino-1 -trans cinnamoylamino-3-methylbutane, m.p. = 149 -1510C; Ho = -°>91 0C (c = 1, methanol). Elemental analysis: calculated: 68.65%C, 8.49%H, 8.49%N; found: 68.69%C, 8.73%H, 9.01%N.IR (KBr) 3359 (NH, urethane), 3326 (N-H, amide), 1688 (C=O, urethane), 1173(C-O, urethane), 964 (=C-H, cinnamoyl), 764 (CH, phenyl), 723 (CH phenyl) [cm"1J.

Reference： [1]Current Patent Assignee: ZULA DIAGNOSTICS - WO2007/129952, 2007, A1 Location in patent: Page/Page column 16

16
[ 6066-82-6 ]
[ 79-08-3 ]
[ 538-75-0 ]
[ 42014-51-7 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	In DCM; at 20℃;	Example 4 2,5-Dioxopyrrolidinyl bromoacetate Bromoacetic acid (4.30g) and N-hydroxysuccinimide (4.03g) were dissolved in DCM (25ml). The mixture was stirred on a magnetic stirrer at room temperature. DCC was added (7.42 g) in one portion and the mixture was reacted overnight. The reaction mixture was filtered to remove dicyclohexylurea. The filter cake was washed several times with DCM. The combined filtrates were washed three times with saturated aqueous sodium chloride solution (30 mL/each wash), dried over anhydrous magnesium sulfate, and filtered. The title compound was obtained as a white solid (5 g) after rotary evaporation in vacuo.

Reference： [1]Patent: EP1867649,2007,A1 .Location in patent: Page/Page column 10-11

17
[ 616-05-7 ]
[ 33069-62-4 ]
2'-(+/-)-2-bromohexanoyl taxol [ No CAS ]
[ 2387-23-7 ]

Reference： [1]Patent: EP1229030,2002,A2 .Location in patent: Example 1

18
[ 485-89-2 ]
[ 2941-20-0 ]
[ 2387-23-7 ]
[ 174636-33-0 ]

Yield	Reaction Conditions	Operation in experiment
		DESCRIPTION 1(S)-(-)-N-(a-ethylbenzyl)-3-hydroxy-2-phenyl-4-quinoline carboxamide 2.49 g (9.4 mmols) of <strong>[485-89-2]3-hydroxy-2-phenyl-4-quinoline carboxylic acid</strong> (CAS [485-89-2]) were suspended in 150 ml of a mixture of THF/MeCN 7:3, respectively; 1.40 g (10.3 mmols) of 1-hydroxybenzotriazole (HOBT) were added to the suspension and then 1.27 g (9.4 mmols) of (S)-(-)-1-phenylpropylamine, dissolved in 20 ml of methylene chloride were added dropwise over 10 minutes period. The reaction mixture was stirred at room temperature for 30 minutes and then 2.13 g (10.3 mmols) of dicyclohexylcarbodiimide (DCC), dissolved in 20 ml of methylene chloride, were added dropwise and the reaction stirred overnight. 20 ml of H2O were added and the reaction stirred 30 minutes, then the solvent was evaporated in vacuo to dryness. The residue was taken up in EtOAc, the precipitated dicyclohexylurea (DCU) was filtered off and the filtrate washed with water, 20% citric acid, 5% NaHCO3, brine and the organic layer dried over Na2SO4 and the solvent evaporated in vacuo. The residue was purified by silica-gel (60-240 mesh) flash column chromatography, eluting with a mixture of hexane/EtOAc 9:1, containing increasing amounts of EtOAc, until the ratio 7:3. The purified product was crystallized from i-PrOH to yield 1.75 g of the title compound as a white solid. C25H22N2O2 M.P.=168-168.4 C. M.W.=382.47 [a]D20=-28.5 (c=0.5, MeOH) Elemental analysis: Calcd. C, 78.51; H, 5.80; N, 7.33; Found C, 78.49; H, 5.84; N, 7.86. I.R. (Kbr): 3370; 1625; 1525 cm-1. 300 MHz 1H-NMR (DMSO-d6): d: 9.80 (s, 1H); 9.11 (d, 1H); 8.00-7.94 (m, 3H); 7.61-7.42 (m, 8H); 7.38 (dd, 2H);.7.28 (dd, 1H); 5.06 (dt, 1H); 1.82 (ddq, 2H); 0.97 (t, 3H). MS (EI; TSQ 700; source 200 C.; 70 eV; 200 A): 382 (M+.); 264; 247; 219.

Reference： [1]Patent: US6355654,2002,B1 .Location in patent: Page column 16

19
[ 914082-12-5 ]
[ 4547-43-7 ]
[ 634197-27-6 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 17.0833h;	A solution of the acid THP ether 17 (0.20 g, 0.73 mmol), methyl 6- hydroxyhexanoate (0.11 g, 0.73 mmol), and [DMAP] (9 mg, 0.073 mmol) in dichloromethane (5 mL) was cooled to [0C] and then a solution [OF DCC] (0.17 g, 0.8 mmol) in [CH2CL2] (0.5 mL) was added dropwise. The reaction mixture was left to stir for 5 minutes before warming to room temperature. After 17 hours the dicyclohexylurea was filtered off washing with dichloromethane. The filtrate was concentrated and the crude product purified by flash chromatography (ether/hexane, 60: 40) to give the ester 20 as a white solid (160 mg).

Reference： [1]Patent: WO2003/104178,2003,A1 .Location in patent: Page 73

20
[ 914082-12-5 ]
[ 629-96-9 ]
[ 634197-26-5 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 17.0833h;	9.c A solution of the acid THP ether 17 (0.20 g, 0.73 mmol), [1-EICOSANOL] (0.20 g, 0.73 mmol) and DMAP (9 mg, 0.073 mmol) in dichloromethane (5 mL) was cooled to [0°C.] A solution [OF DCC] (0.17 g, 0.8 mmol), in [CH2CL2] (0.5 mL) was added dropwise. The reaction mixture was left to stir for 5 minutes and then allowed to warm to room temperature. Stirring was continued for 17 hours and then the reaction mixture was filtered and the dicyclohexylurea by-product was washed with dichloromethane. The filtrate was concentrated and the crude product purified by flash chromatography (ether/hexane, 60: 40) to give the ester 18 as a white solid (250 mg).

Reference： [1]Current Patent Assignee: CORTICAL - WO2003/104178, 2003, A1 Location in patent: Page 71-72

21
[ 3262-72-4 ]
[ 141-43-5 ]
[ 311342-97-9 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In DMF (N,N-dimethyl-formamide) at 0℃; for 13.75h;	1.1.2.1.2.1 1.2. Second Route for the Synthesis of I-152 using N-Protected L-serine; 1.2.1. N-(N-Boc-L-SERYL)-2-AMINOETHANOL (3) A solution comprising 6.15 g (30 mmol) of N-Boc-L-serine (1, Fluka) and 3.45 g of N-hydroxysuccinimide (30 mmol) in 80 ml of DMF is stirred at 0° C. and 6.2 g (30 mmol) of DCC are added. The reaction mixture is maintained at 0° C. for 15 min, then it is allowed to return to ambient temperature and stirring is continued for 1 h 30. 2.75 ml (60 mmol) of ethanolamine are subsequently added. After stirring for 12 h, the DCU formed is filtered off and washed with 2×15 ml of DMF. The combined organic phases are evaporated to dryness under vacuum. The product is isolated from the residual paste by flash chromatography on a silica gel column (Kieselgel Merck 60, 230-400 mesh; eluent: CH2Cl2/MeOH 6%). The expected compound is collected in the form of a gum which crystallizes from an AcOEt/hexane mixture to provide 5.21 g (Yd=70%) of colorless needles. Rf (CH2Cl2/MeOH, 9.3/0.7): 0.23; (CH2Cl2/MeOH/AcOH, 9/0.9/0.1): 0.47. M.p.=74-76° C. [α]D20=-2.2° (c 0.9, CHCl3). [0163] 1H NMR (d6-DMSO) δ ppm: 1.50 (s, 9H, H t-butyl), 3.18-3.29 (m, 2H, NCH2CH2O), 3.45-3.55 (m, 2H, NCH2CH2O), 3.57-3.70 (m, 2H, β CH2 ser), 4.01-4.10 (m, 1H, α H ser), 4.77 (t, J=5.4 Hz, 1H, OH ser), 4.91 (t, J=5.7 Hz, 1H, NCH2CH2OH), 6.71 (d, J=8.2 Hz, 1H, NH ser); 7.86 (t, J=5.5 Hz, 1H, NHCH2). MS: (FAB+/G-T) m/z 745 (3M+H)+, 497 (2M+H)+, 249 (M+H)+. [TABLE-US-00003] Analysis: C10H20N2O5 (248) Calc. %: C 48.39 H 8.06 N 11.29 Found %: 8.57 8.08 11.08

Reference： [1]Current Patent Assignee: COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - US2004/158092, 2004, A1 Location in patent: Page 13

22
[ 3971-31-1 ]
[ 538-75-0 ]
[ 2387-23-7 ]
[ 4355-31-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	In dichloromethane; at 20℃; for 4h;	A solution of dicyclohexylcarbodiimide (200 g, 1.16 mol) in CH2Cl2 (1000 ml) was added dropwise to a suspension of compound from preparation 1 (257 g, 1.25 mol) in CH2Cl2 (550 ml), and the mixture was stirred at room temperature for 4 hours.The precipitated dicyclohexylurea was filtered and washed several times with cold CH2Cl2 (200 ml*3).The combined organic layer was concentrated to give a white solid, which was suspended in MTBE (900 ml).This solid was collected by filtration, washed with MTBE (250 ml), and dried under house vacuum to give the title compound (137 g).The filtrate was concentrated to a residue, which was suspended in MTBE (250 ml) to give another 31 g of anhydride.The total yield was 168 g (94%).m.p. 138-140 C. 1H NMR: (300 MHz, CDCl3) delta 3.06 (m, 2H), 2.25 (d, 1H), 2.11 (m, 2H), 1.65-1.86 (m, 4H), 1.40-1.60 (m, 1H).

Reference： [1]Patent: US2004/10005,2004,A1 .Location in patent: Page 18

23
[ 39897-05-7 ]
[ 655250-09-2 ]
{4-benzyloxycarbonylamino-[4-(2-tert-butyl-6-methoxy-quinolin-8-ylamino)-pentyl-carbamoyl]-butyl}-carbamic acid benzyl ester [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 4h;	57 Typical procedure for the synthesis of ring-substituted protected amino acid quinoline derivatives To an ice cooled stirred solution of ring-substituted N8-(4-amino-1-methylbutyl)-6-methoxy-8-quinolinamine [(free base), 1 mol] and suitably N-protected amino acid (1.1 mol) in dichloromethane (15 mL), 1,3-dicyclohexylcarbodiimide (1.1 mol) was added. Reaction mixture was allowed to attain room temperature and stirring was continued for another 4 h. The reaction mixture was kept in refrigerator overnight and the separated 1,3-dicyclohexylurea (DCU) filtered, and filtrate was concentrated under reduced pressure. Ethyl acetate was added to the residue and the additional quantity of separated DCU was again removed by filtration. The filtrate was washed with saturated sodium bicarbonate solution (3×10 mL) followed by water (2×10 mL), and dried over Na2SO4. The solvent was removed in vacuo to afford the crude product, which was purified by flash column chromatography on silica gel (230-400 mesh) using 2% methanol in chloroform to afford the product. Example 57 [0228] {4-Benzyloxycarbonylamino-4-[2-tert-butyl-6-methoxy-quinolin-8-ylamino)-pentyl-carbamoyl]-butyl}-carbamic acid benzyl ester [0229] Yield: 98%; IR (KBr): 3430 cm-1 (NH), 1714 cm-1 (ester), 1666 cm-1 (amide carbonyl); 1H NMR (CDCl3): δ 7.85 (d, 1H, 4-Ar-H, J=8.6 Hz), 7.42 (d, 1H, 3-Ar-H, J=8.6 Hz) 10H, Ar-H), 6.44 (bs, 1H, NH), 6.29 (s, 3H, 7-Ar-H), 6.24 (s, 1H, 5-Ar-H), 6.12 (bs, 1H, NH), 5.56 (bs, H, NH), 5.50 (bs, 1H, NH), 5.08 (m, 4H, 2×OCH2Ph), 4.36 (bs, 1H, N-CH), 4.23 (bs, 1H, N-CH), 3.88 (s, 3H, OCH3), 3.72 (s, 4H, 2×N-CH2), 3.56 (bs, 1H, N-CH), 3.21 (m, 4H, 2×CH2), 1.55 (m, 4H, 2×CH2), 1.42 (s, 9H, 3×CH3), 1.26 (d, 3H, CH3); 13C NMR (CDCl3): δ 172.61, 171.59, 163.35, 158.73, 156.95, 156.40, 155.90, 144.80, 136.22, 134.99, 133.53, 128.22, 128.22, 128.12, 118.83, 96.61, 91.48, 55.16, 53.50, 52.50, 47.84, 40.43, 39.66, 37.67, 33.83, 29.91, 29.58, 26.05, 25.89, 20.59, 14.19; HRMS (APCI) m/z 698 (M+1).

Reference： [1]Current Patent Assignee: GOVERNMENT OF INDIA; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - US2004/192724, 2004, A1 Location in patent: Page 15-16

24
[ 490-79-9 ]
[ 59-02-9 ]
[ 216210-47-8 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
87 - 88%	With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20℃;	In this example, the preparation of a representative vitamin E gentisic acid conjugate is described. [00061] To 3.5 g gentisic acid (2,5-dihydroxybenzoic acid) in 200 ml dry THF was added dropwise 4.78 g dicyclohexylcarbodiimide (DCC) in THF. This was followed by dropwise addition of 0.56 g 4-dimethylaminopyridine in THF with rapid stirring at room temperature. The solution was allowed to stir for 10 to 15 minutes and then 10 g vitamin E in THF was added to the mixture. The solution was stirred overnight. The resulting solution was filtered with Celite to remove dicyclohexylurea (DCU). The filtrate was concentrated to dryness to yield a brownish, viscous oil (87-88%). The infrared spectrum of the product is shown in FIG. 8.

Reference： [1]Patent: US6858227,2005,B1 .Location in patent: Page/Page column 9

25
[ 98446-49-2 ]
[ 372-09-8 ]
[ 538-75-0 ]
[ 846023-24-3 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	In DMF (N,N-dimethyl-formamide); at 10 - 20℃; for 2h;Product distribution / selectivity;	[0059] A reaction flask was charged with dimethylformamide (DMF) (500 mL), 2,4-dichloro-5-methoxyaniline (100 g, 0.52 mol) and cyanoacetic acid (46.6 g, 0.55 mol). The mixture was cooled to 10 C. in an ice bath. To the cooled mixture was added, dropwise, a solution of N,N' dicyclohexylcarbodiimide (119.1 g, 0.58 mol) in DMF (240 mL) so as to keep the temperature below 15 C. After the addition was completed, cooling was discontinued and the reaction was stirred for 2 hours. The urea by-product was then removed via filtration and the cake was washed twice with DMF. To the filtrate was added 700 mL of water. The solid product emerged from solution. The slurry was cooled to 5 C. and held for at least 30 minutes. The product was collected by filtration and washed with water and then dried in vacuo at 60 C. to give 127.08 g of light tan solid.

Reference： [1]Patent: US2005/43537,2005,A1 .Location in patent: Page/Page column 6

26
[ 506-26-3 ]
[ 56-81-5 ]
[ 2387-23-7 ]
[ 14465-68-0 ]

Yield	Reaction Conditions	Operation in experiment
67%	With dicyclohexyl-carbodiimide In dichloromethane at 20℃;	1.2 2) DCCI method 2.19 g GLA95 (3.15 equiv), 230 mg (1 equiv) glycerol, 153 mg DMAP (0.5 equiv) were stirred in 10 ml DCM under nitrogen. 1.85 g DCCI (3.6 equiv) in 5 ml DCM was added. The reaction mixture was stirred at RT under nitrogen overnight. The DCU formed was filtered and washed with DCM. DCM washed 1 x 5MLS N HC1, water, 5% sodium bicarbonate and water. Dried over magnesium sulphate, filtered and concentrated in vacuo to an oil. This oil was then purified on a silica column using 10% ether in hexane as eluting solvent. 1.47 g (67%) of a slightly cloudy oil was obtained. A sample of this product was trans-esterified and subjected to GC analysis. The product contained 95.8% GLA.

Reference： [1]Current Patent Assignee: UNIVERSITY OF GREENWICH - WO2005/18632, 2005, A1 Location in patent: Page/Page column 23

27
[ 15761-38-3 ]
[ 1563-56-0 ]
(S)-{1-[4-bromo-2-(pyridine-2-carbonyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 8.5h;	{1-[4-Bromo-2-(pyridine-2-carbonyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 124; To a stirred solution of (2-amino-5-bromophenyl)-pyridin-2-yl-methanone 123 (16 g, 57.33 mmol) and the N-Boc-L-alanine 107 (10.92 g, 57.73 mmol) in CH2Cl2 (100 mL) was added dicyclohexylcarbodiimide (DCC) (11.91 g, 57.73 mmol) in CH2Cl2 (60 mL) dropwise, over a 30 min period at 0 C. The reaction mixture was allowed to stir an additional 8 h at rt. The dicyclohexyl urea which formed was filtered off and the filtrate concentrated under reduced pressure. The crude solid 124 was purified by recrystallization from hexane and EtOAc to afford 124 (7.88 g, 81%). mp 208-210 C.; IR (KBr, cm-1) 3332, 2931, 1694, 1507, 1287, 1163; 1H NMR (CDCl3) delta 11.68 (s, 1H), 8.71 (d, J=9.0 Hz, 1H), 7.69 (dd, J=9.0, 2.3 Hz, 1H), 7.55-7.62 (m, 2H), 7.46 (td, J=7.6, 1.4 Hz, 1H), 7.30 (t, J=7.5 Hz, 1H), 7.21 (t, J=9.1 Hz, 1H), 5.13 (b, 1H), 4.37 (b, 1H), 1.51 (d, J=7.2 Hz, 3H), 1.45 (S, 9H). MS (EI) m/e (relative intensity) 449 (M++1, 5), 448 (M+, 5), 376 (10), 329 (20), 304 (100), 228 (25); [alpha]26D=-36.1 (c 0.61, EtOAc).

Reference： [1]Patent: US2006/3995,2006,A1 .Location in patent: Page/Page column 60-61

28
[ 15761-38-3 ]
[ 2835-77-0 ]
[ 872873-91-1 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 8.5h;	[1-(2-Benzoyl-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 109.; To a stirred solution of 2-amino-5-bromobenzophenone 108 (5.73 g, 29.07 mmol) and the N-Boc-L-alanine 107 (5 g, 26.43 mmol) in CH2Cl2 (200 mL) was added dicyclohexylcarbodiimide (DCC) (5.99 g, 29.07 mmol) in CH2Cl2 (100 mL) dropwise, over 30 min at 0° C. The reaction mixture was stirred an additional 8 h at rt. The dicyclohexyl urea which formed was filtered off and the filtrate concentrated under reduced pressure. The crude solid 109 was purified by recrystallization from hexane to afford 109 (7.88 g, 81%). mp 127-129° C.; IR (KBr, cm-1) 3288, 2475, 2352, 1684, 1636, 1576, 1507, 1447, 1264, 1165, 700; 1H NMR (CDCl3) δ 11.48 (s, 1H), 8.67 (d, J=8.22 Hz, 1H), 7.71-7.43 (m, 7H), 7.13-7.08 (m, 1H) 5.06 (br s, 1H), 4.36 (br s, 1H), 1.50 (d, J=7.1 Hz, 3H), 1.44 (s, 9H); MS (EI) m/e (relative intensity) 368 (M+, 6), 295 (10), 225 (27), 224 (79), 197 (83), 196 (77), 167 (15), 145 (46), 144 (88), 126 (17), 105 (38), 88 (94), 77(37), 57 (100); [α]26D=-67.7 (c 0.88, EtOAc).

Reference： [1]Current Patent Assignee: WISYS TECHNOLOGY FOUNDATION INC - US2006/3995, 2006, A1 Location in patent: Page/Page column 56-57

29
[ 15761-38-3 ]
[ 1479-58-9 ]
(S)-{1-[4-bromo-2-(2-fluoro-benzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 8.5h;	{1-[4-Bromo-2-(2-fluoro-benzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 116.; To a stirred solution of <strong>[1479-58-9](2-amino-5-bromophenyl)-(2-fluoro-phenyl)-methanone</strong> (60 g, 204 mmol) 115 and the N-Boc-L-alanine 107 (38.59 g, 204 mmol) in CH2Cl2 (500 mL) was added dicyclohexylcarbodiimide (DCC) (42.09 g, 204 mmol) in CH2Cl2 (200 mL) dropwise, over a 30 min period at 0° C. The reaction mixture was allowed to stir an additional 8 h at rt. The dicyclohexyl urea which formed was filtered off and the filtrate concentrated under reduced pressure. The crude solid residue 116 was purified by recrystallization from hexane and EtOAc to afford 116 (74.9 g, 79percent). mp 158-159° C.; IR (KBr, cm-1) 3332, 2931, 255, 1694, 1643, 1613, 1582, 1537, 1450; 1H NMR (CDCl3) delta 11.68 (s, 1H), 8.71 (d, J=9.0 Hz, 1H), 7.69 (dd, J=9.0, 2.3 Hz, 1H), 7.55-7.62 (m, 2H), 7.46 (td, J=7.6, 1.4 Hz, 1H), 7.30 (t, J=7.5 Hz, 1H), 7.21 (t, J=9.1 Hz, 1H), 5.13 (b, 1H), 4.37 (b, 1H), 1.51 (d, J=7.2 Hz, 3H), 1.45 (S, 9H). MS (EI) m/e (relative intensity) 467 (M++2, 14), 466 (M++1, 44), 465 (M+, 14), 464 (42), 329 (15), 321 (60), 295 (100), 224 (26); [alpha]26D=-59.1 (c 0.51, EtOAc).

Reference： [1]Patent: US2006/3995,2006,A1 .Location in patent: Page/Page column 58-59

30
Boc-(R)-Ala [ No CAS ]
[ 2835-77-0 ]
R-[1-(2-benzoyl-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 8.5h;	1-(2-Benzoyl-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 130; To a stirred solution of 2-amino-5-bromobenzophenone (5.73 g, 29.07 mmol) and the N-Boc-D-alanine 129 (5 g, 26.43 mmol) in CH2Cl2 (200 mL) was added dicyclohexylcarbodiimide (DCC) (5.99 g, 29.07 mmol) in CH2Cl2 (100 mL) dropwise, over a 30 min period at 0° C. The reaction mixture was allowed to stir an additional 8 h at rt. The dicyclohexyl urea which formed was filtered off and the filtrate concentrated under reduced pressure. The crude solid 130 was purified by recrystallization from hexane to afford 130 (7.97 g, 82%). mp 127-129° C.; IR (KBr, cm-1) 3288, 2475, 2352, 1684, 1636, 1576, 1507, 1447, 1264, 1165, 700; 1H NMR (CDCl3) δ 11.48 (s, 1H), 8.67 (d, J=8.22 Hz, 1H), 7.71-7.43 (m, 7H), 7.13-7.08 (m, J=1H) 5.06 (br s, 1H), 4.36 (br s, 1H), 1.50 (d, J=7.1 Hz, 3H), 1.44 (s, 9H); MS (EI) m/e (relative intensity) 368 (M+, 6), 295 (10), 225 (27), 224 (79), 197 (83), 196 (77), 167 (15), 145 (46), 144 (88), 126 (17), 105 (38), 88 (94), 77(37), 57 (100); [α]26D=67.3 (c 0.44, EtOAc).

Reference： [1]Current Patent Assignee: WISYS TECHNOLOGY FOUNDATION INC - US2006/3995, 2006, A1 Location in patent: Page/Page column 62-63

31
[ 3744-87-4 ]
[ 1479-58-9 ]
(R)-{1-[4-bromo-2-(2-fluoro-benzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 8.5h;	{1-[4-Bromo-2-(2-fluorobenzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 136; To a stirred solution of (2-amino-5-bromophenyl)-(2'-fluoro-phenyl)-methanone 115 (60 g, 204 mmol) and the N-Boc-D-alanine 129 (38.59 g, 204 mmol) in CH2Cl2 (500 mL) was added dicyclohexylcarbodiimide (DCC) (42.09 g, 204 mmol) in CH2Cl2 (200 mL) dropwise, over a 30 min period at 0° C. The reaction mixture was allowed to stir an additional 8 h at rt. The dicyclohexyl urea which formed was filtered off and the filtrate concentrated under reduced pressure. The crude solid product 136 was purified by recrystallization from hexane and EtoAc to afford 136 (73 g, 77percent). mp 158-159° C.; IR (KBr, cm-1) 3332, 2931, 255, 1694, 1643, 1613, 1582, 1537, 1450; 1H NMR (CDCl3) delta 11.68 (s, 1H), 8.71 (d, J=9.0 Hz, 1H), 7.69 (dd, J=9.0, 2.3 Hz, 1H), 7.55-7.62 (m, 2H), 7.46 (td, J=7.6, 1.4 Hz, 1H), 7.30 (t, J=7.5 Hz, 1H), 7.21 (t, J=9.1 Hz, 1H), 5.13 (b, 1H), 4.37 (b, 1H), 1.51 (d, J=7.2 Hz, 3H), 1.45 (S, 9H). MS (EI) m/e (relative intensity) 467 (M++2, 14), 466 (M++1, 44), 465 (M+, 14), 464 (42), 329 (15), 321 (60), 295 (100), 224 (26); [alpha]26D=59.6 (c 0.51, EtOAc).

Reference： [1]Patent: US2006/3995,2006,A1 .Location in patent: Page/Page column 65-66

32
[ 98642-18-3 ]
[ 2921-20-2 ]
[ 538-75-0 ]
1,3-di-(tert-butyloxycarbonylamino)-2-[(tetradecylthio)acetylthio]-propane [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
72%	With dmap In dichloromethane at 20℃; for 20h;	15 Preparation of 1,3-di(tert-butyloxycarbonylamino)-2-(tetradecylthioacetylthio) propane (example 15d) 1,3-[di(tert-butoxycarbonylamino)]-2-mercaptopropane (example 15c) (0.295 g, 0.963 mmol) was dissolved in dichloromethane (40 ml). Dicyclohexylcarbodiimide (0.199 g, 0.963 mmol), dimethylaminopyridine (0.118 g, 0.963 mmol) and tetradecylthioacetic acid (example 1) (0.278 g, 0.963 mmol) were then added. The reaction mixture was stirred at room temperature and the progress of the reaction was monitored by TLC. After 20 hours of reaction, the dicyclohexylurea precipitate was filtered, washed with dichloromethane and the filtrate was evaporated. The residue obtained (0.73 g) was purified by chromatography on silica gel (eluent:dichloromethane) to give the desired comopund in the form of a white powder. Yield: 72% Rf (dichloromethane/ethyl acetate 95:5): 0.29 IR: νNH 3328 cm-1; νCO thioester 1717 cm-1; νCO carbamate 1687 cm-1 MP: 47-51° C. NMR (1H, CDCl3): 0.88 (t, 9H, CH3, J=6.1 Hz); 1.26 (multiplet, 22H, -CH2-); 1.44 (s, 18H, CH3 (BOC)); 1.53-1.65 (m, 2H, -CH2-CH2-S-CH2-CO); 2.59 (t, 2H, -CH2-CH2-S-CH2-COS-, J=7.8 Hz); 3.21-3.30 (m, 2H, BOCNH-CHaHb--CH-CHaHb-NHBOC); 3.40 (s, 2H, CH2-S-CH2-COS-); 3.42-3.49 (m, 2H, BOCNH-CHaHb-CH-CHaHb-NHBOC); 3.62-3.65 (m, 1H, BOCNH-CH2-CH-CH2-NHBOC); 5.24 (multiplet, 2H, -NHBOC). MS (MALDI-TOF): M+23=599 (M+Na+); M+39=615 (M+K+)

Reference： [1]Current Patent Assignee: SA GENFIT - US2006/69156, 2006, A1 Location in patent: Page/Page column 25

33
[ 2921-20-2 ]
methyl 2,3-diaminopropanoate dihydrochloride [ No CAS ]
[ 538-75-0 ]
methyl 2,3-di[(tetradecylthio)acetyl]amino}propanoate [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With benzotriazol-1-ol; triethylamine In dichloromethane at 0 - 20℃; for 49h;	13 Preparation of methyl 2.3-ditetradecylthioacetylaminopropanoate (example 13b) Methyl 2,3-diaminopropanoate dihydrochloride (example 13a) (0.500 g, 2.62 mmol) and tetradecylthioacetic acid (example 1) (1.51 g, 5.23 mmol) were dissolved in dichloromethane (80 ml) at 0° C. followed by the addition of triethylamine (0.79 ml), dicyclohexylcarbodiimide (1.62 g, 7.85 mmol) and hydroxybenzotriazole (0.707 g, 5.23 mmol). The reaction medium was stirred at 0° C. for 1 hour then brought to room temperature for 48 hours. The dicyclohexylurea precipitate was filtered and washed with dichloromethane and the filtrate was evaporated. The residue obtained (3.68 g) was purified by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 95:5) to give the desired compound in the form of a white powder. Yield: 96% Rf: (dichloromethane/methanol 98:2): 0.63 IR: νNH amide 3276 cm-1; νCO ester 1745 cm-1; νCO amide 1649 cm-1 MP: 81.5-82.5° C. NMR (1H, CDCl3): 0.89 (t, 6H, CH3, J=6.6 Hz); 1.26-1.37 (multiplet, 44H, -CH2-); 1.56-1.61 (m, 4H, -CH2-CH2-S-CH2-CONH); 2.50-2.60 (m, 4H, -CH2-CH2-S-CH2-CONH-); 3.22 (s, 2H, -CH2-S-CH2-CONH-); 3.25 (s, 2H, -CH2-S-CH2-CONH-); 3.74 (m, 2H, H3CO(CO)-CH-CH2-NHCO-); 3.79 (s, 3H, -COOCH3); 4.64-4.70 (m, 1H, H3CO(CO)-CH-CH2-NHCO-); 7.79 (d, 2H, -NHCO-, J=7.3 Hz). MS (MALDI-TOF): M+1=659 (M+H+); M+23=681 (M+Na+); M+39=697 (M+K+)

Reference： [1]Current Patent Assignee: SA GENFIT - US2006/69156, 2006, A1 Location in patent: Page/Page column 23-24

34
1,3-diamino-2-[(tetradecylthio)acetyloxy]-propane dihydrochloride [ No CAS ]
[ 2921-20-2 ]
[ 538-75-0 ]
1,3-di-[(tetradecylthio)acetyl]amino}-2-[(tetradecylthio)acetyloxy]-propane [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
74%	With benzotriazol-1-ol; triethylamine In dichloromethane at 0 - 20℃; for 49h;	11 Preparation of 1,3-ditetradecylthioacetylamino-2-(tetradecylthioacetyloxy)propane 1,3-diamino-2-tetradecylthioacetyloxypropane dihydrochloride (example 10) (0.400 g, 0.92 mmol) and tetradecylthioacetic acid (example 1) (0.532 g, 1.84 mmol) were dissolved in dichloromethane (50 ml) at 0° C. followed by the addition of triethylamine (0.3 ml, 2.1 mmol), dicyclohexylcarbodiimide (0.571 g, 2.77 mmol) and hydroxybenzotriazole (HOBt) (0.249 g, 1.84 mmol). The reaction medium was stirred at 0° C. for 1 hour then brought to room temperature for 48 hours. The dicyclohexylurea precipitate was filtered and washed with dichloromethane. The filtrate was vacuum evaporated. The residue obtained (1.40 g) was purified by chromatography on silica gel (eluent: dichloromethane followed by dichloromethane/ethyl acetate 9:1). Yield: 74% Rf (dichloromrthane/ethyl acetate 8:2): 0.25 IR: νNH 3279, 3325 cm-1; νCO ester 1731 cm-1; νCO amide 1647, 1624 cm-1 MP: 87-89° C. NMR (1H, CDCl3): 089 (t, 9H, CH3, J=6.6 Hz); 1.26 (multiplet, 66H, -CH2-); 1.55-1.60 (multiplet, 6H, -CH2-CH2-S-CH2-CO); 2.55 (t, 4H, -CH2-CH2-S-CH2-CONH-, J=7.2 Hz); 2.65 (t, 2H, -CH2-CH2-S-CH2-COO-, J=7.2 Hz); 3.21 (s, 2H, -CH2-S-CH2-COO-); 3.25 (s, 4H, -CH2-S-CH2-CONH-); 3.40-3.49 (m, 2H, -CONH-CHaHb-CH-CHaHb-NHCO-); 3.52-3.61 (m, 2H, -CONH-CHaHb-CH-CHaHb-NHCO-); 4.96 (m,1H, -CONH-CH2-CH-CH2-NHCO-); 7.42 (multiplet, 2H, -NHCO-). MS (MALDI-TOF): M+1=901 (M+H+); M+23=923 (M+Na+); M+39=939 (M+K+)

Reference： [1]Current Patent Assignee: SA GENFIT - US2006/69156, 2006, A1 Location in patent: Page/Page column 23

35
2,3-di-[(tetradecylthio)acetyl]amino}-propan-1-ol [ No CAS ]
[ 2921-20-2 ]
[ 538-75-0 ]
2,3-di-[(tetradecylthio)acetyl]amino}-1-[(tetradecylthio)acetyloxy]-propane [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
59%	With dmap In tetrahydrofuran at 20℃; for 20h;	14 Preparation of 2.3-ditetradecylthioacetylamino-1-tetradecylthioacetyloxypropane 2,3-ditetradecylthioacetylaminopropan-1-ol (example 13) (0.200 g, 0.32 mmol) was dissolved in tetrahydrofuran (40 ml) followed by the addition of dicyclohexylcarbodiimide (65 mg, 0.32 mmol), dimethylaminopyridine (39 mg, 0.32 mmol) and tetradecylthioacetic acid (example 1) (91 mg, 0.32 mmol). The mixture was stirred at room temperature for 20 hours. The dicyclohexylurea precipitate was filtered, washed with tetrahydrofuran and the filtrate was evaporated. The residue obtained (1 g) was purified by flash chromatography (eluent:dichloromethane) to produce the desired compound in the form of a white powder. Yield: 59% Rf: (dichloromethane/ethyl acetate 8:2): 0.49 IR: νNH amide 3281 cm-1; νCO ester 1736 cm-1; νCO amide 1641 cm-1 MP: 95.4-97.3° C. NMR (1H, CDCl3): 0.89 (t, 9H, CH3, J=6.4 Hz); 1.27-1.34 (multiplet, 66H, -CH2-); 1.54-163 (m, 6H, -CH2-CH2-S-CH2-CO-); 2.53 (t, 4H, -CH2-CH2-S-CH2-CONH-, J=7.2 Hz); 2.65 (t, 2H, -CH2-CH2-S-CH2-COO-, J=7.2 Hz); 3.21 (s, 2H, -CH2-S-CH2-CONH-); 3.23 (s, 2H, -CH2-S-CH2-CONH-); 3.25 (s, 2H, -CH2-S-CH2-COO-); 3.46-3.56 (m, 2H, -OCO-CH2-CH-CH2-NHCO-); 4.22-4.25 (m, 2H, -OCO-CH2-CH-CH2-NHCO-); 4.29-4.39 (m, 1H, -OCO-CH2-CH-CH2-NHCO-); 7.29 (t, 1H, -NHCO-); 7.38 (d, 1H, -NHCO-, J=7.6 Hz). MS (MALDI-TOF): M+1=901 (M+H+)

Reference： [1]Current Patent Assignee: SA GENFIT - US2006/69156, 2006, A1 Location in patent: Page/Page column 24

36
1,3-diamino-2-[(tetradecylthio)acetylthio]-propane dihydrochloride [ No CAS ]
[ 2921-20-2 ]
[ 538-75-0 ]
1,3-di-[(tetradecylthio)acetyl]amino}-2-[(tetradecylthio)acetylthio]-propane [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With benzotriazol-1-ol; triethylamine In dichloromethane at 0 - 20℃; for 49h;	16 Preparation of 1.3-ditetradecylthioacetylamino-2-(tetradecylthioacetylthio)propane 1,3-diamino-2-tetradecylthioacetylthiopropane dihydrochloride (example 15) (100 mg, 0.225 mmol) and tetradecylthioacetic acid (example 1) (130 mg, 0.450 mmol) were dissolved in dichloromethane (30 ml) at 0° C. followed by the addition of triethylamine (68 μl), dicyclohexylcarbodiimide (139 mg, 0.675 mmol) and hydroxybenzotriazole (61 mg, 0.450 mmol). The reaction mixture was stirred at 0° C. for 1 hour then brought to room temperature for 48 hours. The dicyclohexylurea precipitate was filtered and washed with dichloromethane and the filtrate was evaporated. The residue obtained (430 mg) was purified by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 95:5) to give the desired compound in the form of a white powder. Yield: 82% Rf (dichloromethane/methanol 98:2): 0.54 IR: νCO thioester 1660 cm-1; νCO amide 1651 cm-1 MP: 83-85° C. NMR (1H, CDCl3): 0.89 (t, 9H, CH3, J=6.6 Hz); 1.26 (multiplet, 66H, -CH2-); 1.56-1.62 (multiplet, 6H, -CH2-CH2-S-CH2-CO); 2.56 (t, 4H, -CH2-CH2-S-CH2-CONH-, J=7.5 Hz); 2.61 (t, 2H, -CH2-CH2-S-CH2-COS-, J=7 Hz); 3.26 (s, 4H, CH2-S-CH2-CONH-); 3.42 (s, 2H, CH2-S-CH2-COS-); 3.44-3.49 (m, 2H, -CONH-CHaHb-CH-CHaHb-NH-CO); 3.55-3.61 (m, 2H, -CONH-CHaHb-CH-CHaHb-NHCO-); 3.70-3.71 (m,1H, BOCNH-CH2-CH-CH2-NHBOC); 7.58-7.62 (m, 2H, NHCO). MS (MALDI-TOF): M+1=917 (M+H+); M+23=939 (M+Na+)

Reference： [1]Current Patent Assignee: SA GENFIT - US2006/69156, 2006, A1 Location in patent: Page/Page column 25-26

37
1-amino-2-[(tetradecylthio)acetyl]oxy-3-[(tetradecylthio)acetyl]thio-propane hydrochloride [ No CAS ]
[ 2921-20-2 ]
[ 538-75-0 ]
1-[(tetradecylthio)acetyl]amino-2-[(tetradecylthio)acetyl]oxy-3-[(tetradecylthio)acetyl]thio-propane [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With benzotriazol-1-ol; triethylamine In dichloromethane at 0 - 20℃; for 49h;	23 Preparation of 1-tetradecylthioacetylamino-2-tetradecylthiacetyloxy-3-tetradecylthioacetylthioproPane 3-amino-2-tetradecylthioacetyloxy-1-tetradecylthioacetyl-thiopropane hydrochloride (example 22) (100 mg, 0.15 mmol) and tetradecylthioacetic acid (example 1) (63 mg, 0.22 mmol) were dissolved in dichloromethane (30 ml) at 0° C. followed by the addition of triethylamine (0.044 ml), dicyclohexylcarbodiimide (60 mg, 0.29 mmol) and hydroxybenzotriazole (30 mg, 0.22 mmol). The reaction medium was stirred at 0° C. for 1 hour then brought to room temperature for 48 hours. The dicyclohexylurea precipitate was filtered, washed with dichloromethane and the filtrate was evaporated. The residue obtained (263 mg) was purified by flash chromatography (eluent: dichloromethane/ethyl acetate 98:2) to give the desired compound in the form of a white powder. Yield: 98% Rf (dichloromethane/ethyl acetate 95:5): 0.38 IR: νNH amide 3340 cm-1; νCO ester 1727 cm-1; νCO amide and thioester 1655 and 1669 cm-1 MP: 63.9-67.1° C. NMR (1H, CDCl3): 0.89 (t, 9H, CH3, J=6.2 Hz); 1.26 (multiplet, 66H, -CH2); 1.54-1.66 (m, 6H, -CH2-CH2-S-CH2-CO-); 2.52-2.67 (m, 6H, -CH2-CH2-S-CH2-CO-); 3.08 (m, 1H, -S-CH2-CH-CH2-NHCO or -S-CH2-CH-CH2-NHCO); 3.21 (s, 2H, CH2-S-CH2-CONH-); 3.23 (s, 2H, CH2-S-CH2-COO-); 3.27 (m, 1H, -S-CH2-CH-CH2-NHCO or -S-CH2-CH-CH2-NHCO); 3.43 (s, 2H, CH2-S-CH2-COS-); 3.50 (m, 1H, -S-CH2-CH-CH2-NHCO or -S-CH2-CH-CH2-NHCO); 3.62 (m, 1H, -S-CH2-CH-CH2-NHCO or -S-CH2-CH-CH2-NHCO); 5.06 (m, 1H, -COS-CH2-CH-CH2-NHCO); 7.24 (t,1H, -NHCO, J=6.7 Hz) MS (MALDI-TOF): M+1=918 (M+H+); M+23=940 (M+Na+)

Reference： [1]Current Patent Assignee: SA GENFIT - US2006/69156, 2006, A1 Location in patent: Page/Page column 30

38
[ 19622-83-4 ]
3,4-cyclic phosphate sodium 7-deoxynarcistatin [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With pyridine; tetrabutylammonium dihydrogen phosphate; dicyclohexyl-carbodiimide at 80℃; for 48h;	Sodium 7-Deoxy-narcistatin (8). A solution of 7-deoxy-narciclasine (2c, 0.2 g, 0.69 mmol) in pyridine (8 ml) was heated to 80 °C and tetrabutylammonium dihydrogen phosphate (0.15 g, 0.45 mmol, 0.65 equiv) followed by dicyclohexylcarbodiimide (0.8 g, 5.6 equiv) were added. The reaction was allowed to proceed at 80 °C for 24 hours. An 1H NMR analysis of the reaction mixture composition indicated a 50:50 mixture of starting material to product. Tetrabutylammonium dihydrogen phosphate (0.15 g) was added followed by DCCI (0.8 g) and the reaction continued for a further 24 hours. At this point, 1H NMR analysis of a sample from the reaction mixture showed reaction was complete. The reaction mixture was cooled and water (100 ml) was added. The precipitated dicyclohexylurea (DCU) was collected and the pyridine- water mother liquor was concentrated to minimum volume. The aqueous fraction was then passed through an ion exchange column (DOWEX 50W8-400) in the sodium form. The UV responsive fractions were combined and lypholized to yield phosphate 8 as a colorless solid: 227 mg (88%); mp 255 °C (dec).

Reference： [1]Current Patent Assignee: ARIZONA BOARD OF REGENTS - WO2006/76726, 2006, A1 Location in patent: Page/Page column 15

39
[ 29477-83-6 ]
[ 2387-23-7 ]
3,4-cyclic phosphate sodium narcistatin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With pyridine; tetrabutylammonium dihydrogen phosphate; dicyclohexyl-carbodiimide at 80℃; for 120h;	Method for Synthesis of Sodium Narcistatin (11). Synthesis of 3,4-cyclic phosphate 11 from narciclasine (2a) (0.113 g, 0.368 mmol) was carried out in pyridine (4 ml) using tetrabutylammonium dihydrogen phosphate (0.075 g, 0.22 mmol) and dicyclohexylcarbodiimide EPO (0.4 g, 1.94 mmol), with additional amounts of tetrabutylanimonium dihydrogen phosphate (0.185 g) and dicyclohexylcarbodiimide (0.4 g) added after about the first 24 hours stirring at about 80 °C. The reaction is stirred for about 96 hours, cooled and filtered to remove precipitated dicyclohexylurea (DCU). Water (100 ml) is added and the mixture refiltered to remove any residual DCU. The mother liquor is concentrated to minimum volume. The aqueous fraction is eluted through an ion exchange column (sodium form). The UV active fractions are combined and lypholized to yield the phosphate 11 as a cream solid (88% yield). Rather than eluting the aqueous fraction via a sodium form of an ion exchange column, another suitable salt form (such as potassium or lithium) could be used to produce a compound such as potassium narcistatin or lithium narcistatin.

Reference： [1]Current Patent Assignee: ARIZONA BOARD OF REGENTS - WO2006/76726, 2006, A1 Location in patent: Page/Page column 11-12

40
[ 18274-81-2 ]
[ 22494-42-4 ]
2',4'-difluoro-4-hydroxy-[1,1'-biphenyl]-3-carboxylic acid 4-(3H-1,2-dithiole-3-thione-5-yl)-phenyl ester [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 20h;	2 A IN solution of dicyclohexylcarbodiimide (DCC) in dichloromethane (455 mg, 2.2 mmol) was added to 100 ml of a dichloromethane solution containing of 5- (p- hydroxyphenyl) -3H-1, 2-dithiol-3-thione (451.2 mg, 1.99 mmol) , prepared as described in example 1, diflunisal (500 mg, 1.99 mmol) and 4-dimethylaminopyridine (DMAP) (245 mg, 1.99 mmol) .The mixture was stirred at room temperature under nitrogen for 20 hours. At the end of the reaction dicyclohexylurea (DCU) was removed by filtration.The solution was washed with 0. IN NaOH and cold water. The organic solution was then dried on anhydrous sodium sulphate and evaporated. After removal of the solvent, the mixture was chromatographed on silica gel eluting with a mixture of dichloromethane/ methanol(99.5/0.5) .The compound after washing first with ether, then with ethanol and crystallization with ethyl acetate had a melting point of 202-204 0C

Reference： [1]Current Patent Assignee: C T G PHARMA - WO2006/111791, 2006, A1 Location in patent: Page/Page column 10

Yield	Reaction Conditions	Operation in experiment
72.0%		The solvent was distilled off under reduced pressure and to the residue thus obtained 1N sodium hydroxide (150 ml) was added. The mixture was stirred for 3 hours at 30 C. The thus precipitated N,N'-dicyclohexylurea was separated by filtration, and the filtrate was adjusted to pH 2.5 with 6N hydrochloric acid and was extracted twice with chloroform (200 ml). The chloroform layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The thus obtained residue was dissolved in 50% methanol (300 ml), and-hydrogen gas was passed through the solution in the presence of 2% palladium-carbon as a catalyst for 2 hours at 40 C. The catalyst was separated by filtration and the solvent was distilled off under reduced pressure The residue thus obtained was recrystallized from water and ethanol to give L-alanyl-L-proline (13.41 g; 72.0%). NMR spectrum [D2 O, Internal standard TSP] ppm 1.50 (t,3H), 1.71-2.50 (m,4H), 3.35-3.75 (m,2H) 4.05 (q,0.6H), 4.12-4.45 (m,1.4H).

42
[ 2921-20-2 ]
[ 502-52-3 ]
[ 538-75-0 ]
1,3-di-O-dipalmitoyl-2-O-tetradecylthioacetylglycerol [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With imethylaminopyridine In dichloromethane at 20℃; for 72h;	4.4g Preparation of 1,3-dipalmitoyl-2-tetradecylthioacetylglycerol 1,3-dipalmitoylglycerol (example 3a) (5.64 g, 9.9 mmol, 1 eq), tetradecylthioacetic acid (example 1a) (5.74 g, 19.8 mmol, 2 eq), dicyclohexylcarbodiimide (4.1 g, 19.8 mmol, 2 eq) and dimethylaminopyridine (2.42 g, 19.8 mmol, 2 eq) were dissolved in dichloromethane. The reaction mixture was stirred at room temperature for 3 days. The dicyclohexylurea which formed was filtered and washed several times with dichloromethane. The filtrate was dried. The residual product was purified by silica gel chromatography (eluent:dichloromethane/cyclohexane 4:6). Yield: 80% Rf (dichloromethane/cyclohexane 7:3): 0.32 MP: 60-62° C. IR: νCO ester 1744 and 1730 cm-1 NMR (1H, CDCl3): 0.86-0.91 (t, 9H, -CH3, J=6.6 Hz); 1.10-1.45 (multiplet, 70H, -CH2-); 1.57-1.64 (multiplet, 6H, -CH2-CH2-CH2-S- and OCOCH2-CH2); 2.30-2.35 (t, 4H, OCOCH2-CH2-, J=7.4 Hz); 2.60-2.66 (t, 2H, CH2-CH2-S-, J=7.4 Hz); 3.23 (s, 2H, S-CH2-COO); 4.14-4.21 (dd, 2H, -CHaHb-CH-CHaHb-, J=12 Hz and J=5.8 Hz); 4.30-4.36 (dd, 2H, -CHaHb-CH-CHaHb-, J=12 Hz and J=4 Hz); 5.26-5.33 (m, 1H, -CHaHb-CH-CHaHb-) MS (MALDI-TOF): M+23=861 (M+Na+); M+39=877 (M+K+)

Reference： [1]Current Patent Assignee: SA GENFIT - US2006/252827, 2006, A1 Location in patent: Page/Page column 16

43
[ 2921-20-2 ]
[ 538-75-0 ]
[ 56-81-5 ]
GFT-14 [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With dimethylaminopyridine In dichloromethane at 20℃; for 48h;	4.4a Example 4a Preparation of 1,2,3-tritetradecylthioacetylglycerol Glycerol (1 g, 10.86 mmol) was dissolved in dichloromethane (200 ml). Dicyclohexylcarbodiimide (7.84 g, 38.01 mmol), dimethylaminopyridine (4.64 g, 38.01 mmol) and tetradecylthioacetic acid (example 1a) (9.40 g, 32.58 mmol) were then added. The mixture was stirred at room temperature. After 48 hours of reaction, the dicyclohexylurea precipitate was filtered, washed with dichloromethane and the filtrate was evaporated. The residue obtained was purified by silica gel chromatography (eluent:dichloromethane/cyclohexane 4:6). 1,2,3-tritetradecylthioacetylglycerol was obtained as a white powder. Yield: 65% Rf (dichloromethane/cyclohexane 7:3): 0.47 MP: 57° C. IR: νCO ester 1738 and 1722 cm-1 NMR (1H, CDCl3): 0.89 (t, 9H, -CH3, J=6.5 Hz); 1.26 (multiplet, 66H, -CH2-); 1.62 (m, 6H, -CH2-CH2-CH2-S-); 2.63 (t, 6H, CH2-CH2-S-, J=7.3 Hz); 3.23 (s, 6H, S-CH2-COO); 4.27 (dd, 2H, -CHaHb-CH-CHaHb-, J=12 Hz and J=6 Hz); 4.39 (dd, 2H, -CHaHb-CH-CHaHb-, J=12 Hz and J=4.3 Hz); 5.34 (m, 1H, -CHaHb-CH-CHaHb-) MS (MALDI-TOF): M+23=925 (M+Na+); M+39=941 (M+K+)

Reference： [1]Current Patent Assignee: SA GENFIT - US2006/252827, 2006, A1 Location in patent: Page/Page column 15

44
[ 497263-42-0 ]
[ 2921-20-2 ]
[ 538-75-0 ]
2-N-tetradecylthioacetamido-1,3-di-O-ditetradecylthioacetyloxypropane [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
66%	With dimethylaminopyridine In dichloromethane at 20℃; for 48h;	5.5b Example 5b Preparation of 2-tetradecylthioacetamido-1,3-ditetradecylthioacetyloxypropane 2-tetradecylthioacetamidopropan-1,3-diol (example 5a) (1 g, 2.77 mmol) was dissolved in dichloromethane (180 ml). Dicyclohexycarbodiimide (1.427 g, 6.91 mmol), dimethylaminopyridine (0.845 g, 6.91 mmol) and tetradecylthioacetic acid (example 1a) (1.995 g, 6.91 mmol) were then added in that order. The reaction mixture was stirred at room temperature for 48 hours. The dicyclohexylurea precipitate was filtered and washed with dichloromethane and the filtrate was concentrated. The residue obtained was purified by silica gel chromatography (eluent:dichloromethane/cyclohexane 7:3). The desired compound was obtained as a white powder. Yield: 66% RF (dichloromethane): 0.18 MP: 82-84° C. IR: νCO ester 1715 and 1730 cm-1; νCO amide 1648 cm-1 NMR (1H, CDCl3): 0.84-0.95 (t, 9H, -CH3, J=6.6 Hz); 1.22-1.45 (multiplet, 66H, -CH2-); 1.54-1.69 (multiplet, 6H, -CH2-CH2-CH2-S-); 2.48-2.55 (t, 2H, CH2-CH2-S-CH2-CONH-, J=7.5 Hz); 2.59-2.70 (t, 4H, CH2-CH2-S-CH2-COO-, J=7.2 Hz); 3.24 (s, 6H, S-CH2-CO-); 4.18-4.35 (multiplet, 4H, -CH2-CH-CH2-); 4.47-4.60 (m, 1H, -CH2-CH-CH2-); 7.23 (d, 1H, -CONH-, J=8.5 Hz). MS (MALDI-TOF): M+23=924 (M+Na+)

Reference： [1]Current Patent Assignee: SA GENFIT - US2006/252827, 2006, A1 Location in patent: Page/Page column 19

45
[ 2387-23-7 ]
[ 2438-38-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; sulfur trioxide; In 1,2-dichloro-ethane;	EXAMPLE 3 224 parts of N,N'-dicyclohexylurea are suspended in 2,000 parts by volume of 1,2-dichloroethane. 104 parts of SO3 (100% strength by weight) are added in the course of 60 minutes, at 50 C. This produces a clear solution, which is heated until it refluxes, and 98 parts of sulfuric acid (100% strength by weight) are then added. CO2 is evolved and cyclohexylamidosulfonic acid precipitates. Yield: 345 parts (96.4% of theory) of cyclohexylamidosulfonic acid of melting point 168 C.

Reference： [1]Patent: US4117004,1978,A

46
[ 941-37-7 ]
[ 2387-23-7 ]
1-N-cyclohexylamino-3,5-dimethyl-adamantane hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%		EXAMPLE 8 1-N-cyclohexyl-3,5-dimethyl-adamantane hydrochloride 2.43 grams of <strong>[941-37-7]1-bromo-3,5-dimethyl adamantane</strong> and 1.86 grams of N,N'-dicyclohexylurea were heated to 190 C. in a closed vessel for 45 minutes. The cooled product was worked up as in Example 5. 1.52 Grams of 1-N-cyclohexylamino-3,5-dimethyl-adamantane hydrochloride was isolated. Yield: 51% of the theoretical yield.

Reference： [1]Patent: US4122193,1978,A

47
[ 872187-37-6 ]
[ 538-75-0 ]
[ 100-51-6 ]
[ 918157-07-0 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
88.6%	With dmap In dichloromethane at 0 - 20℃; for 2.5h;	1.II Step II; Preparation of 2-tert-butoxycarbonylamino-3-[4-(4-formylphenoxy)-phenyl]-propionic acid benzyl ester (3); 2-N-t-Butoxycarbonyl-3-[4-(4-formylphenoxy)phenyl)]propionic acid, 2, (4.3 g, 11.16 mmol) was dissolved in dichloromethane (30 mL) and cooled to 0-5° C. N,N'-Dicyclohexylcarbodiimide (3.0 g, 14.5 mmol), anhydrous benzyl alcohol (1.2 mL, 11.16 mmol) and finally 4-dimethylaminopyridine (0.27 g, 2.23 mmol) were added and the resulting mixture was stirred at that temperature under an atmosphere of argon. After 30 min, the reaction mixture was warmed up to room temperature and stirring was continued. After 2 h, the reaction mixture was cooled in an ice bath to precipitate out the side product N,N'-dicyclohexylurea that was filtered and the clear filtrate was concentrated under vacuum. The resulting oil was dissolved in ethyl acetate (2×100 mL), washed with 10% citric acid (1×100 mL), water (1×100 mL) and brine (1×100 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield the crude product. This crude material was purified by silica gel flash chromatography using toluene-ethyl acetate (93:7) mixture to yield the benzyl ester 3 (4.7 g, 88.6%). 1H NMR (DMSO-d6): 9.91 (s, 1H), 7.89 (d, J=8.0 Hz, 2H), 7.42 (d, J=8.4 Hz, 2H), 7.31-7.43 (m, 7H), 7.06 (d, J=8.8 Hz, 2H), 7.05 (d, J=8.4 Hz, 2H), 5.12 (s, 2H), 4.23-4.29 (m, 1H), 3.05 (dd, J=13.6 and 5.2 Hz, 1H), 2.91 (dd, J=14.0 and 10.2 Hz, 1H), 1.33 (s, 9H).

Reference： [1]Current Patent Assignee: ORCHID PHARMA LTD - US2007/4776, 2007, A1 Location in patent: Page/Page column 12

48
[ 54060-30-9 ]
[ 119389-05-8 ]
N-(3-ethynylphenyl)-4'-phenylethynylphthalisoimide [ No CAS ]
[ 2387-23-7 ]

Reference： [1]Patent: WO2006/137369,2006,A1 .Location in patent: Page/Page column 30

49
[ 623-57-4 ]
[ 1510-21-0 ]
[ 926890-44-0 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
34%	With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 6.25h;Product distribution / selectivity;	To a solution of 3-dimethylamino-l,2-propanediol (0.5g, 3,6 mmoles) in 10 mL dichloromethane was added cholesterylhemisuccinic acid (1.75g, 3.6 mmoles) and DCC (1.48g, 7.2 mmoles) at 0°C. The reaction was allowed to proceed from 0°C (15 mins) to room temperature for 6 hours. DCU was filtered off and the filtrate was evaporated on a rotary evaporator and loaded on a silica gel (230-400 mesh). The desired product was EPO <DP n="57"/>eluted with 4-5percent methanol in chloroform (v/v) to give a colorless thick liquid (0.834g, Rf -0.5 in 10percent methanol in chloroform, yield 34percent).1HNMR (400 MHz, CDCl3): delta 5.36 (d, J= 4.0 Hz, IH), 4.67-4.56 (m, IH), 4.19 (dd, J= 11.6, 3.6 Hz, IH), 4.04 (dd, J= 11.6, 6.0 Hz, IH), 3.97-3.89 (m, IH), 2.70-2.56 (m, 4H), 2.44 (t, J= 10.0 Hz, IH), 2.36-2.23 (m, 9H), 2.05-1.75 (m, 5H), 1.66-0.80 (m, 33H), 0.67 (s, 3H).
34%	With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 6.08333h;Product distribution / selectivity;	An alternative synthesis procedure is as follows: to an ice-cooled solution of cholesteryl hemisuccinate (4.09 g, 8.42 mmol) in DMF (35 mL) 3-(dimethylamino)-l,2- propandiol (1.0 mL, 8.42 mmol) was added N,N'-dicyclohexylcarbodiimide (3.47 g, 16.84 mmol). After 5 min., the ice bath was removed and the solution was stirred for an additional 6 h at room temperature. The resulting precipitation of dicyclohexylurea was removed by filtration. The filtrate was transferred to a 100 mL round bottom flask and concentrated to dryness under vacuum. The pasty mass was dissolved in CHCl3 (200 mL) and washed with H2O (30 mL), saturated aqueous NaCl (30 mL), dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography (SiO2, elution with 5percent MeOH in CHCl3) furnished IV (1.68 g, 34percent) as wax. NMR spectra coordinates are as follows: 1H NMR (CDCl3): delta 5.36 (d, J= 4.0 Hz, IH), 4.67-4.56 (m, IH), 4.19 (dd, J = 11.6, 3.6 Hz, IH), 4.04 (dd, J= 11.6, 6.0 Hz, IH), 3.97-3.89 (m, IH), 2.70-2.56 (m, 4H), 2.44 (t, J= 10.0 Hz, IH), 2.36-2.23 (m, 9H), 2.05-1.75 (m, 5H), 1.66-0.80 (m, 33H), 0.67 (s, 3H).

Reference： [1]Patent: WO2007/22030,2007,A2 .Location in patent: Page/Page column 55-56; 5/17
[2]Patent: WO2007/22030,2007,A2 .Location in patent: Page/Page column 56; 5/17

50
[ 59178-92-6 ]
[ 96-53-7 ]
[ 538-75-0 ]
N-methacryloyl-6-amino hexanoic acid thiazolidine-2-thione [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
78%		N-methacryloyl-6-aminohexanoic acid (3.0 g, 0.015 mol) and 2-thiazoline-2-thiol (1.8g, 0.015 mol) are dissolved in 35 mL of tetrahydrofurane (THF). DCC (3.72g, 0.018 mol) is dissolved in THF (5 mL). Both solutions were cooled down to -15 C. The cooled solutions are mixed and kept for 1 hour at -15 C and then overnight at 5C. The reaction mixture is stirred for 1 hour at room temperature, and then 0.1 mL of acetic acid is added. Mixture is stirred for 1 hour. The precipitated N,N'-dicyclohexylurea (DCU) is filtered off. The solution is evaporated in vacuum and diluted with ethyl acetate. The second part of DCU is removed by filtration. The solution is evaporated in vacuum and diethyl ether is added and product crystallised at 15 C. Product was filtered off, washed with diethyl ether and dried in vacuum. Yield : 3.56 g (78%). (m.p. 61-62 C, elemental analysis: Calcd/found C 51.98/52.03, H 6.72/6.53, N 9.33/9.34, S 21.35/21.10)

Reference： [1]Patent: EP1647283,2006,A1 .Location in patent: Page/Page column 6

51
[ 13726-67-5 ]
[ 32213-95-9 ]
[ 121-44-8 ]
[ 554-68-7 ]
[ 2387-23-7 ]
[ 167082-77-1 ]

Yield	Reaction Conditions	Operation in experiment
64.5%		<strong>[13726-67-5]Boc-Asp-OH</strong> (1.475 g, 6.33 mmol), HCl.Asp-(OMe)2 (2.5 g, 12.66 mmol) and Et3N (1.77 mL, 6.33 mmol) are mixed in 50 mL of tetrahydrofurane (THF) and suspension is cooled to -10C. The DCC (3.12 g, 15.1 mmol) is dissolved in 20 mL THF and the solution is cooled to -10C. Cool solution of DCC in THF is added to the suspension and the reaction mixture is left one hour at -10C and then overnight at 5C without mixing. Reaction mixture is warmed up to room temperature, acetic acid (0.1 mL) is added and a mixture is stirred for 30 min at room temperature. Precipitated N,N'-dicyclohexylurea (DCU) and triethylamine hydrochloride (Et3N.HC1) are filtered off, and a filtrate is concentrated on vacuum evaporator. Oily residue is diluted with ethyl acetate (100 mL) and gradually extracted with 2 wt% aqueous sodium hydrogen carbonate (50 mL), 0.5 wt% citric acid (50 mL) and water (50 mL) in a last step. Organic layer is dried with sodium sulfate and product is crystallized from a mixture ethyl acetate/hexane. Yield: 2.1g (64.5%), m.p. 115-116C, TLC: (silica gel, ethyl acetate, Rf = 0.54). Elemental analysis: Calcd/found C = 48.55/48.85, H = 6.40/6.50, N = 8.09/8.05. The Boc protection group is removed by trifluoroacetic acid (TFA). Boc-Asp-[Asp-(OMe)2]2 (2.0 g) is dissolved in TFA (8.0 mL) and stirred for 30 min at room temperature. The excess of TFA is evaporated, the mixture was tree times diluted with dry methanol and the solvent evaporated again. The oilly residue is triturated with diethyl ether to form crystals of TFA.Asp-[Asp-(OMe)2]2. Yield 1.6 g (77.9%)

Reference： [1]Patent: EP1647283,2006,A1 .Location in patent: Page/Page column 5-6

52
[ 2038-03-1 ]
[ 944159-19-7 ]
[ 38194-50-2 ]
[ 944159-16-4 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	With Succinimide; dicyclohexyl-carbodiimide; In pyridine; for 48h;	<strong>[38194-50-2]Sulindac</strong> (100 mg, 0.28 mmol) is dissolved in anhydrous pyridine (5 mL) under an argon atmosphere. DCC (86.66 mg, 0.42 mmol), NHS (48.34 mg, 0.42 mmol) and the amine (0.044 mL, 0.34 mmol) are added sequentially to the solution, and the reaction mixture is stirred for 2 days. The reaction is quenched by the addition of deionized water (5 mL). The precipitated material (mostly N,N'-dicyclohexylurea) is removed by filtration, and the mixture is evaporated on a rotary evaporator. The residue is co-evaporated with toluene to remove residual pyridine. The crude product is purified by column chromatography (60-200 mesh) and pure compound is dried overnight under vacuum then at 78 0C for 4 hours. The crude product is purified by column chromatography using CHCb/MeOH (95:5). Yellow solid, 75% yield. ESI-MS m/z: 469 [M+H]+. 1H NMR (DMSO-d6): zeta 8.00 (IH5 1, J= 5.0 Hz5 NHCH2CH2), 7.79 (2H, d, J= 8.5 Hz, 3'-H, 5'-H), 7.71 (2Eta, d, J= 8.2 Hz, 2'-H& 6'-H), 7.35 (IH5 s, 8-H), 7.15 (1Eta, dd, J= 5.2 Hz, 8.4 Hz, 7-H)5 7.10 (1Eta, dd, J= 2.4 Hz5 9.4 Hz, 4- <n="15"/>H), 6.71 (1Eta, ddd, J= 2.5 Hz5 9.6 Hz, 11.1 Hz5 6-H), 3.52 (4Eta, t, J= 4.6 Hz3 3"-H, 4"-H)5 3.43(2Eta, s, 1-CH2), 3.21-3.15 (2Eta, m, -NHCH2CH2 ), 2.82 (3H5 s, 4'-CH3), 2.35-2.30(6Eta, m, 2"-H, 5"-H, -NHCH2CH2), 2.18(3Eta, S, 2-CH3). CEtaN Found: C, 65.81 ; Eta, 5.95; N, 5.83. Calcd. for C26H29FN2O3S ? 0.4 H2O; C5 65.64; H5 6.31; N, 5.89.

Reference： [1]Patent: WO2007/81694,2007,A2 .Location in patent: Page/Page column 10; 12-13

53
[ 92953-12-3 ]
[ 114798-26-4 ]
[ 538-75-0 ]
[ 1070175-00-6 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In tetrahydrofuran; at 20℃; for 5h;	Step 2 A solution of dicyclohexylcarbodiimide (DCC) (463mg; 1.2 eq.) in anhydrous tetrahydrofurane (THF) was added dropwise to a solution of losartan (800 mg; 1.67 mmol), 3-methanesulfonylsulfanyl-propionic acid (1.87 mmol) prepared as above described and dimethylaminopyridine (DMAP, 13 mg) in 19 ml of anhydrous THF. The reaction was performed at room temperature, stirring under nitrogen for 5 hours. At the end of the reaction, the dicyclohexylurea (DCU) was removed by filtration. The solution was evaporated to dryness and the residue was chromatographed on a silica gel column, eluding with a mixture of CH2Cl2-methanol (98:2) to give the desired compound.

Reference： [1]Patent: EP1980559,2008,A1 .Location in patent: Page/Page column 10

54
[ 18274-81-2 ]
[ 538-75-0 ]
[ 124750-92-1 ]
[ 1070174-98-9 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In tetrahydrofuran; at 20℃; for 5h;	Step 3:; A solution of dicyclohexylcarbodiimide (DCC) (267.4 mg; 1.3 eq.) in anhydrous THF (10 ml) was added dropwise to a stirred solution of losartan acid (472 mg; 1.08 mmol) prepared as described in step 2, 5-(4-hydroxyphenyl)-3H-1,2-dithiol-3-thione (244.5 mg; 1.08 mmol) prepared as above described (step 1) and dimethylaminopyridine (DMAP, 7 mg) in 15 ml of tetrahydrofurane (THF). The reaction is performed at room temperature, stirring under nitrogen for 5 hours. At the end of the reaction the dicyclohexylurea (DCC) is removed by filtration. The solution is evaporated to dryness and the crude product was purified by column chromatography (on silica gel) eluting with CH2C12-methanol (97:3) to give an orange solid with melting point 180-185 C.

Reference： [1]Patent: EP1980559,2008,A1 .Location in patent: Page/Page column 9

55
[ 13700-08-8 ]
[ 538-75-0 ]
[ 124750-92-1 ]
[ 1070174-99-0 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In tetrahydrofuran; at 20℃; for 5h;	Step 2:; A solution of dicyclohexylcarbodiimide (DCC) (267.4 mg; 1.3 eq.) in anhydrous THF (10 ml) was added dropwise to a stirred solution of losartan acid (472 mg; 1.08 mmol) prepared as described in EXAMPLE 2, step 2, methanethiosulfonic acid S-(2-hydroxyethyl) ester (1.08 mmol) prepared as above described (step 1) and dimethylaminopyridine (DMAP, 7 mg) in 15 ml of tetrahydrofurane (THF). The reaction is performed at room temperature, stirring under nitrogen for 5 hours. At the end of the reaction the dicyclohexylurea (DCC) is removed by filtration. The solution is evaporated to dryness and the crude product was purified by column chromatography (on silica gel) eluting with CH2Cl2-methanol (98:2) to give the desired product with a melting point of 105-110 C.

Reference： [1]Patent: EP1980559,2008,A1 .Location in patent: Page/Page column 10

56
[ 114798-26-4 ]
[ 538-75-0 ]
[ 127588-56-1 ]
[ 1070174-97-8 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In tetrahydrofuran; at 20℃; for 5h;	Step 2:; A solution of dicyclohexylcarbodiimide (DCC) (463mg; 1.2 eq.) in anhydrous tetrahydrofurane (THF) was added dropwise to a solution of losartan (800 mg; 1.67 mmol), 4-(3-thioxo-3H-1,2-dithiol-4-yl)benzoic acid (475.6 mg; 1.87 mmol) prepared as above described and dimethylaminopyridine (DMAP, 13 mg) in 19 ml of anhydrous THF. The reaction was performed at room temperature, stirring under nitrogen for 5 hours. At the end of the reaction, the dicyclohexylurea (DCU) was removed by filtration. The solution was evaporated to dryness and the residue was chromatographed on a silica gel column, eluting with a mixture of CH2Cl2-methanol (98:2) to give a compound with m.p. 218-222 C.

Reference： [1]Patent: EP1980559,2008,A1 .Location in patent: Page/Page column 9

57
[ 6066-82-6 ]
[ 112-79-8 ]
[ 538-75-0 ]
OL-HPR [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 0 - 5℃;	The exemplary conjugates in Figs 4 A-F, to which reference is now made, were synthesized according to the procedure elaborated infra. A solution of fatty acid (FA) (1.5 mol) and N-hydroxysuccinimide (1.6 mmol) in dry dichloromethane is cooled in an ice-water bath and dicylohexylcarbomiimide (1.6 mol) is added with stirring. The mixture is kept in the refrigerator (between 0 and +5 0C) overnight. The separated N1N'- dicyclohexylurea is removed by filtration and the solvent evaporated in vacuum. The crude product is twice recrystalized from isopropanol

Reference： [1]Current Patent Assignee: MEDWELL LAB; MEDWELL LABORATORIES - WO2008/75366, 2008, A2 Location in patent: Page/Page column 7

58
[ 3417-91-2 ]
[ 538-75-0 ]
[ 74-11-3 ]
[ 254899-76-8 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
95.3%	In dichloromethane at 20℃; Inert atmosphere;	19.1 Preparation Procedures:; (1); In a reaction flask were mixed an intermediate M-29 (2.31 g, 10 mmol), 4-chlorobenzoic acid (1.57 g, 10 mmol), DCC (2.47 g, 12 mmol) and DMAP (200 mg, as a catalyst). To the mixture was added anhydrous CH2Cl2 (150 ml). The reaction mixture was stirred overnight under nitrogen at room temperature. The resulting precipitate dicyclohexylurea (DCU) was removed by filtering on the morrow. The filtrate was evaporated to dryness to recover the solvents. The resulting solid was dissolved with ethyl acetate (100 ml). The solution was washed in turn with distilled water, diluted hydrochloric acid (40 ml), distilled water, 5% NaHCO3 (40 ml) and saturated aqueous NaCl (40 ml) and dried over anhydrous sodium sulfate. The solution was evaporated under reduced pressure to dryness to recover ethyl acetate, giving an intermediate M-75-Ome (3.18 g, 95.3%) as a white foam.

Reference： [1]Current Patent Assignee: 302 MILITARY HOSPITAL CHINA; TIANJIN INSTITUTE OF PHARMACEUTICAL RESEARCH; GUIZHOU MEDICAL UNIVERSITY - US2009/247470, 2009, A1 Location in patent: Page/Page column 17-18

59
[ 82717-96-2 ]
[ 87269-87-2 ]
[ 538-75-0 ]
[ 2387-23-7 ]
[ 87269-88-3 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; triethylamine; In dichloromethane; at 25 - 30℃; for 16h;	Example 6. Preparation of benzyl ramipril; 40 gms of (S,S,S)-2-azabicyclo[3.3.0]-octane-3-carboxylic acid benzyl ester hydrochloride was charged in a round bottom flask to this 40 gms of triethylamine,26gms of l-hydroxybenzotriazole,46 gms of N-[l-(S)-(ethoxy carbonyl)-3-phenylpropyl]-L- alanine, 33 gms of N,N dicyclohexyl carbodimide and 700ml of dichloromethane were added. The reaction mixture was stirred at 25-30 C for 16 hrs. Dicyclohexyl urea precipitated out and was removed by filteration.The filtrate was washed with 1200ml of water followed by distillation of solvent to obtain benzyl ramipril as oil. Yield=71.9gm

Reference： [1]Patent: WO2009/122433,2009,A2 .Location in patent: Page/Page column 13

60
(5-{5-methyl-[1,2,4]oxadiazol-3-yl}-1-oxo-1,3-dihydro-isoindol-2-yl)-acetic acid [ No CAS ]
[ 538-75-0 ]
[ 40004-08-8 ]
(4-{2-[5-(5-methyl-[1,2,4]oxadiazol-3-yl)-1-oxo-1,3-dihydro-isoindol-2-yl]-acetyl}-piperazin-1-yl)-acetic acid ethyl ester [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: (5-{5-methyl-[1,2,4]oxadiazol-3-yl}-1-oxo-1,3-dihydro-isoindol-2-yl)-acetic acid; dicyclohexyl-carbodiimide With benzotriazol-1-ol In DMF (N,N-dimethyl-formamide) at 0℃; for 0.166667h; Stage #2: 1-(Ethoxycarbonylmethyl)piperazine In DMF (N,N-dimethyl-formamide) at 0℃;	66e DCC (0.433g ; 2.1 mmol) was added with vigorous stirring to a solution of the compound of example 66d (0.53g ; 1.9 mmol) and 1-hydroxybenzotriazole (0.338g ; 2.47 mmol) in dry DMF (15 ml) at 0°C. After 10 min. piperazin-1-yl-acetic acid ethyl ester (0.43g ; 2.47 mmol) was added to the mixture It was stirred at 0°C for lh and then kept in the freezer over night. The DCU was filtered off and the filtrate was washed with IN aqueous NaHC03, water, IN aqueous HC1, brine, dried (Na2SO4), concentrated and purified using flash chromatography (silica gel, 5% MeOH in chloroform) to obtain the title compound. Yield, 0.64g (77%); mp, 189-90°C ; MS (ESI+) : 450 (M++Na), analysis: C2lH25N505 requires C, 59.01 ; H, 5.90 ; N, 16.38 ; found: C, 58. 80 ; H, 5.93 ; N, 15.80%.

Reference： [1]Current Patent Assignee: PIRAMAL ENTERPRISES LIMITED - WO2005/35495, 2005, A2 Location in patent: Page/Page column 128

61
[ 29713-96-0 ]
[ 167844-03-3 ]
[ 850399-96-1 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
73.6%	Stage #1: N,O-bis-(benzyloxycarbonyl)-L-tyrosine With benzotriazol-1-ol; dicyclohexyl-carbodiimide In ethyl acetate at 0℃; for 0.166667h; Stage #2: ethyl 2-(4-piperidyloxy)-acetate In DMF (N,N-dimethyl-formamide); ethyl acetate at 0℃; for 18h;	67d DCC (4.12g ; 20 mmol) in EtOAc (10 ml) was added under vigorous stirring to a solution of di-Z-L-Tyr (8. 08g ; 18 mmol) and HOBt (2.7g ; 20 mmol) in EtOAc (100 ml) at 0°C. After 10 min, the compound of example 67c (4.46g ; 19.93 mmol) was neutralized with Et3N (2. 8 ml; 20 mmol) in DMF (10 ml) at 0°C and was added to the reaction mixture. The resulting mixture was stirred at 0°C for 2h and then kept in the freeze over night (-16h). DCU was filtered off. The filtrate was successively washed with IN NaHC03, water, IN HC1 and brine. It was dried over anhydrous Na2SO4. The solvent was removed. The crude product was purified by flash chromatography with 10% CH3CN in CHC13. Yield, 8.2g (73.6%) ; MS (ESI): 641 (M++Na), 619 (M++1) ; analysis: C34H38N209 requires: C, 66.01 ; H, 6.19 ; N, 4.53 ; found: C, 66.39 ; H, 6.58 ; N, 4. 81%.

Reference： [1]Current Patent Assignee: PIRAMAL ENTERPRISES LIMITED - WO2005/35495, 2005, A2 Location in patent: Page/Page column 129-130

62
[ 2450-71-7 ]
[ 58-85-5 ]
[ 773888-45-2 ]
[ 2387-23-7 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 5416 - 5424

63
[ 1823-59-2 ]
[ 10526-07-5 ]
[ 119389-05-8 ]
poly(4,4'-oxydiphthalic acid dianhydride-co-1,3-bis(3-aminophenoxy)benzene-co-4-phenylethynylphthalic anhydride) [ No CAS ]
[ 2387-23-7 ]

Reference： [1]Patent: WO2006/137369,2006,A1 .Location in patent: Page/Page column 33

64
[ 141-43-5 ]
[ 538-75-0 ]
[ 135321-95-8 ]
tert-butyl 4-hydroxy-3-[(2-hydroxyethyl)amino]carbonyl}phenylcarbamate [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: dicyclohexyl-carbodiimide; 2-hydroxy-5-<(tert-butoxycarbonyl)amino>benzoic acid With 1-hydroxy-pyrrolidine-2,5-dione In 1,4-dioxane at 0 - 20℃; for 24.5h; Stage #2: ethanolamine In 1,4-dioxane at 20℃; for 72h;	5 To a solution of 5-(BOC-amino)salicylic acid (7.59 g, 30 mM) and N- hydroxysuccinimide (3.7 g, 32 mM) in dry dioxane (100 ml) cooled to O0C was added 1,3-dicyclohexylcarbodiimide (6.6 g, 32 mM) in five portions over 30 min. The cooling bath was removed and the reaction mixture was stirred at r.t. for 24 hrs. 2-Hydroxyethylamine (2.0 g, 33 mM) was added and the reaction mixture was stirred at r.t. for 3 days. Ethyl acetate was added and the λ/,λ/'-dicyclohexyl- urea was filtered off and washed with ethyl acetate (2 x 200 ml). The filtrate was washed with water, dried over MgSO4, filtered and the solvents were removed under vacuum. The residue was crystallized from ethyl acetate (45 ml) and hexane (75 ml) to give tert-butyl 4-hydroxy-3-[(2-hydroxyethyl)amino] carbonyl}phenylcarbamate (7.61 g, 86%) as a colorless solid. 1H-NMR (DMSO- d6): 11.71 (s, IH), 9.10 (s, IH), 8.67 (t, J = 5.4 Hz, IH), 7.89 (d, J=2 Hz, IH), 7.29 (dd, J=8.9, 2.0 Hz, IH), 6.81 (d, J=8.9 Hz, IH), 4.79 (t, J = 5.1 Hz, IH), 3.50 (q, J = 6.0 Hz, 2H), 3.34 (q, J = 5.4 Hz, 2H).

Reference： [1]Current Patent Assignee: PHARMA IP - WO2007/65261, 2007, A1 Location in patent: Page/Page column 38-39

65
[ 1246269-69-1 ]
[ 2493-84-7 ]
[ 1246269-72-6 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
62%	With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 12h;

Reference： [1]Location in patent: experimental part Al-Hamdani, Uhood J.; Gassim, Tarik E.; Radhy, Howraa H. [Molecules, 2010, vol. 15, # 8, p. 5620 - 5628]

66
[ 104115-82-4 ]
[ 2493-84-7 ]
[ 1246269-74-8 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
52%	With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 12h;

Reference： [1]Location in patent: experimental part Al-Hamdani, Uhood J.; Gassim, Tarik E.; Radhy, Howraa H. [Molecules, 2010, vol. 15, # 8, p. 5620 - 5628]

67
[ 16434-26-7 ]
[ 2493-84-7 ]
[ 1246269-75-9 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
45%	With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 12h;

Reference： [1]Location in patent: experimental part Al-Hamdani, Uhood J.; Gassim, Tarik E.; Radhy, Howraa H. [Molecules, 2010, vol. 15, # 8, p. 5620 - 5628]

68
[ 124-38-9 ]
[ 108-91-8 ]
[ 109-73-9 ]
[ 1792-17-2 ]
[ 2158-01-2 ]
[ 2387-23-7 ]

Reference： [1]Green Chemistry,2010,vol. 12,p. 1811 - 1816

69
[ 542-52-9 ]
[ 2387-23-7 ]
[ 17671-80-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With silica gel-supported lanthanum(III) oxide at 150℃; for 6h; Autoclave; Inert atmosphere;

Reference： [1]Location in patent: experimental part Guo, Xiaoguang; Shang, Jianpeng; Li, Jian; Wang, Liguo; Ma, Yubo; Shi, Feng; Deng, Youquan [Synthetic Communications, 2011, vol. 41, # 8, p. 1102 - 1111]

70
[ 17090-79-8 ]
[ 112-35-6 ]
[ 1297518-94-5 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
64%	With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane at -10 - 20℃;	2.2.3. Synthesis of M-AM4 amide A solution of MONA (1000 mg, 1.49 mmol), 3,6,9-trioxadecylamine (653 mg, 4.00 mmol) and 1,3-dicyclohexylcarbodiimide (DCC) (515 mg, 2.50 mmol), all dissolved in 25 cm3 dichloromethane and 1-hydroxybenzotriazole (HOBt) (330 mg, 2.44 mmol) dissolved in 10 cm3 tetrahydrofuran were mixed together and stirred at a temperature between 0 °C and -10 °C for 24 h. After this time the reaction mixture was stirred at room temperature for the next 24 h. The solvents were evaporated under reduced pressure to dryness. The residue was dissolved in 2:1 dichloromethane-hexane mixture and filtered off to remove 1,3-dicyclohexylurea as a by-product. The filtrate was evaporated under reduced pressure and purified by chromatography on silica gel (Fluka type 60) to give M-AM4 (778 mg, 64% yield) as a colourless solid glass state.

Reference： [1]Location in patent: experimental part Łowicki, Daniel; Huczyński, Adam; Brzezinski, Bogumil; Bartl, Franz [Journal of Molecular Structure, 2011, vol. 990, # 1-3, p. 121 - 131]

71
[ 22966-25-2 ]
[ 2387-23-7 ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2011,vol. 26,p. 422 - 429

72
[ 10238-21-8 ]
[ 16673-34-0 ]
[ 2387-23-7 ]

Reference： [1]Magnetic Resonance in Chemistry,2012,vol. 50,p. 246 - 255

73
[ 10238-21-8 ]
[ 2387-23-7 ]

Reference： [1]Magnetic Resonance in Chemistry,2012,vol. 50,p. 246 - 255

74
[ 67-66-3 ]
[ 108-91-8 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With oxygen; sodium hydrogencarbonate; triethylamine In water for 1h; Irradiation;
62%	With oxygen; sodium hydroxide In water at 20℃; for 3h; Irradiation;	18; 26 Example 17: Synthesis of 1,3-Diphenylurea General procedure: Purified chloroform (20 mL), aniline (0.93 g, 10 mmol) and sodium hydroxide aqueous solution (NaOH: 4 g, 20 mL) were added to the above-described reaction vessel, and the mixture was stirred to be mixed. Oxygen gas was blown into the stirred reaction mixture at a flow rate of 0.5 L/min at 20° C. to cause bubbling, and a light was irradiated from the low pressure mercury lamp. After 2 hours, dichloromethane and water were added to the reaction mixture, and an organic phase and a water phase were separated. The organic phase was dried by anhydrous sodium sulfate and then concentrated under reduced pressure. The thus obtained black solid was recrystallized by using dichloromethane and n-hexane to obtain black powder (yield amount: 0.13 g, yield: 12%). The obtained solid was analyzed by 1H-NMR; as a result, it was confirmed that the target compound was generated.

Reference： [1]Kuwahara, Yuki; Zhang, Ailing; Soma, Haruka; Tsuda, Akihiko [Organic Letters, 2012, vol. 14, # 13, p. 3376 - 3379]
[2]Current Patent Assignee: MITSUBISHI GAS CHEMICAL COMPANY INC; KOBE UNIVERSITY - US2020/79723, 2020, A1 Location in patent: Paragraph 0153-0156; 0167; 0170-0171

75
[ 124-38-9 ]
[ 108-91-8 ]
[ 16033-71-9 ]
3-cyclohexyl-4-methyloxazolidin-2-one [ No CAS ]
2-hydroxypropyl 1-cyclohexylcarbamate [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 47.1% 2: 26.7% 3: 9.9%	With sodium iodide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate In tetrahydrofuran at 150℃; for 2h;	Example 2 Preparation of DCU and HPCC Through Reaction at High Pressure Cyclohexylamine (CHA, also “CyNH2”) (4.26 g, 43 mmol), propylene oxide (PO) (43 mmol, 2.5 g), [Bmim][InCl4] (0.085 g, 0.215 mmol), NaI (0.161 g, 1.075 mmol) and tetrahydrofuran (THF) (15 mL) as a solvent were added to a 100-mL high-pressure reactor equipped with a magnetic stirrer. After performing reaction for 2 hours under a CO2 pressure of 1200 psig at 150° C., the reaction mixture was cooled to room temperature. After adding a predetermined amount (2 mL) of external standard, the solid product was separated. The separated solid product was washed 2-3 times with distilled water to remove cyclohexyl carbamate salt (CyNH3+CyNHCOO-). After further washing 2-3 times with THF, the product was completely dried in a vacuum oven. After the drying, the produced dicyclohexylurea (N,N′-dicyclohexylurea, DCU) was weighed to calculate the production yield of DCU. The conversion rate (%) of CHA and the yield of DCU were calculated according to Equation 1 and Equation 2. The residue remaining after the separation of the solid product was analyzed by gas chromatography (GC) equipped with a flame ionization detector (FID) to confirm the production of hydroxypropyl N-(cyclohexyl)carbamate (HPCC), aminoalcohol (CyNHCH2CHCH3OH, AmA) and 3-cyclohexyl-4-methyloxazolidone (CMOxz). The yields of HPCC, AmA and CMOxz were calculated using the external standard. According to the GC analysis result, the CHA conversion rate was 85.9%, the DCU yield was 47.1%, the HPCC yield was 26.7%, the CMOxz yield was 9.9%, and the AmA yield was 2.1%.

Reference： [1]Current Patent Assignee: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGY - US2015/133676, 2015, A1 Location in patent: Paragraph 0061; 0062

76
[ 124-38-9 ]
[ 108-91-8 ]
[ 16033-71-9 ]
[ 103-00-4 ]
3-cyclohexyl-4-methyloxazolidin-2-one [ No CAS ]
2-hydroxypropyl 1-cyclohexylcarbamate [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 45.9% 2: 9% 3: 8.6% 4: 20.4%	With sodium iodide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate In tetrahydrofuran at 150℃; for 2h;	Examples 17 Cyclohexylamine (CHA, also “CyNH2”) (4.26 g, 43 mmol), propylene oxide (PO) (43 mmol, 2.5 g), [Bmim][InCl4] (0.085 g, 0.215 mmol), NaI (0.161 g, 1.075 mmol) and tetrahydrofuran (THF) (15 mL) as a solvent were added to a 100-mL high-pressure reactor equipped with a magnetic stirrer. After performing reaction for 2 hours under a CO2 pressure of 1200 psig at 150° C., the reaction mixture was cooled to room temperature. After adding a predetermined amount (2 mL) of external standard, the solid product was separated. The separated solid product was washed 2-3 times with distilled water to remove cyclohexyl carbamate salt (CyNH3+CyNHCOO-). After further washing 2-3 times with THF, the product was completely dried in a vacuum oven. After the drying, the produced dicyclohexylurea (N,N′-dicyclohexylurea, DCU) was weighed to calculate the production yield of DCU. The conversion rate (%) of CHA and the yield of DCU were calculated according to Equation 1 and Equation 2. The residue remaining after the separation of the solid product was analyzed by gas chromatography (GC) equipped with a flame ionization detector (FID) to confirm the production of hydroxypropyl N-(cyclohexyl)carbamate (HPCC), aminoalcohol (CyNHCH2CHCH3OH, AmA) and 3-cyclohexyl-4-methyloxazolidone (CMOxz). The yields of HPCC, AmA and CMOxz were calculated using the external standard. According to the GC analysis result, the CHA conversion rate was 85.9%, the DCU yield was 47.1%, the HPCC yield was 26.7%, the CMOxz yield was 9.9%, and the AmA yield was 2.1%.Experiment was conducted under the same condition as in Example 2 while varying the ionic liquid. The result is shown in Table 4. As seen from Table 4, when [Bmim]-based ionic liquid was used, CHA conversion rate and DCU yield were increased and the production of reaction byproducts such as AmA was suppressed. In Example 23, the amount of CHA was 2 times that of Example 2. It can be seen that the result was better when the equivalence ratio of CHA to PO was 1 than when it was 2.
1: 20.9% 2: 16.6% 3: 8.5% 4: 30.6%	With sodium bromide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate In tetrahydrofuran at 150℃; for 2h;	7 Examples 7 Cyclohexylamine (CHA, also “CyNH2”) (4.26 g, 43 mmol), propylene oxide (PO) (43 mmol, 2.5 g), [Bmim][InCl4] (0.085 g, 0.215 mmol), NaI (0.161 g, 1.075 mmol) and tetrahydrofuran (THF) (15 mL) as a solvent were added to a 100-mL high-pressure reactor equipped with a magnetic stirrer. After performing reaction for 2 hours under a CO2 pressure of 1200 psig at 150° C., the reaction mixture was cooled to room temperature. After adding a predetermined amount (2 mL) of external standard, the solid product was separated. The separated solid product was washed 2-3 times with distilled water to remove cyclohexyl carbamate salt (CyNH3+CyNHCOO-). After further washing 2-3 times with THF, the product was completely dried in a vacuum oven. After the drying, the produced dicyclohexylurea (N,N′-dicyclohexylurea, DCU) was weighed to calculate the production yield of DCU. The conversion rate (%) of CHA and the yield of DCU were calculated according to Equation 1 and Equation 2. The residue remaining after the separation of the solid product was analyzed by gas chromatography (GC) equipped with a flame ionization detector (FID) to confirm the production of hydroxypropyl N-(cyclohexyl)carbamate (HPCC), aminoalcohol (CyNHCH2CHCH3OH, AmA) and 3-cyclohexyl-4-methyloxazolidone (CMOxz). The yields of HPCC, AmA and CMOxz were calculated using the external standard. According to the GC analysis result, the CHA conversion rate was 85.9%, the DCU yield was 47.1%, the HPCC yield was 26.7%, the CMOxz yield was 9.9%, and the AmA yield was 2.1%. Experiment was conducted under the same condition as in Example 2 while varying the promoter, i.e., the alkali metal halide. The result is shown in Table 3. As seen from Table 3, when LiI, NaI, KI, RbI or CsI was used as the promoter, there was no significant difference in HPCC and CMOxz yields, but CHA conversion rate and DCU yield were increased and the production of reaction byproducts such as AmA was suppressed. The DCU yield was the highest when NaI was used as the promoter.

Reference： [1]Current Patent Assignee: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGY - US2015/133676, 2015, A1 Location in patent: Paragraph 0061; 0062; 0066
[2]Current Patent Assignee: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGY - US2015/133676, 2015, A1 Location in patent: Paragraph 0061; 0062; 0065

77
[ 124-38-9 ]
[ 108-91-8 ]
[ 16033-71-9 ]
[ 103-00-4 ]
2-hydroxypropyl 1-cyclohexylcarbamate [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 13.4% 2: 14.1% 3: 41.8%	With potassium carbonate; 1-(n-butyl)-3-methylimidazolium tetrachloroindate In tetrahydrofuran at 150℃; for 2h;	Cyclohexylamine (CHA, also “CyNH2”) (4.26 g, 43 mmol), propylene oxide (PO) (43 mmol, 2.5 g), [Bmim][InCl4] (0.085 g, 0.215 mmol), NaI (0.161 g, 1.075 mmol) and tetrahydrofuran (THF) (15 mL) as a solvent were added to a 100-mL high-pressure reactor equipped with a magnetic stirrer. After performing reaction for 2 hours under a CO2 pressure of 1200 psig at 150° C., the reaction mixture was cooled to room temperature. After adding a predetermined amount (2 mL) of external standard, the solid product was separated. The separated solid product was washed 2-3 times with distilled water to remove cyclohexyl carbamate salt (CyNH3+CyNHCOO-). After further washing 2-3 times with THF, the product was completely dried in a vacuum oven. After the drying, the produced dicyclohexylurea (N,N′-dicyclohexylurea, DCU) was weighed to calculate the production yield of DCU. The conversion rate (%) of CHA and the yield of DCU were calculated according to Equation 1 and Equation 2. The residue remaining after the separation of the solid product was analyzed by gas chromatography (GC) equipped with a flame ionization detector (FID) to confirm the production of hydroxypropyl N-(cyclohexyl)carbamate (HPCC), aminoalcohol (CyNHCH2CHCH3OH, AmA) and 3-cyclohexyl-4-methyloxazolidone (CMOxz). The yields of HPCC, AmA and CMOxz were calculated using the external standard. According to the GC analysis result, the CHA conversion rate was 85.9%, the DCU yield was 47.1%, the HPCC yield was 26.7%, the CMOxz yield was 9.9%, and the AmA yield was 2.1%. Experiment was conducted under the same condition as in Example 2 while varying the promoter. The result is shown in Table 2. As seen from Table 2, when NaI was used as the promoter, there was no significant difference in HPCC and CMOxz yields, but CHA conversion rate and DCU yield were increased and the production of reaction byproducts such as AmA was suppressed. However, when other promoters were used, no ionic liquid-based catalyst was used (Comparative Example 14), or no main catalyst was used and only NaI was used (Comparative Example 15), DCU yield was very low and the production of reaction byproducts such as AmA was increased.
1: 41.2% 2: 25.2% 3: 14.4%	With potassium iodide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate In tetrahydrofuran at 150℃; for 2h;	10 Examples 10 Cyclohexylamine (CHA, also “CyNH2”) (4.26 g, 43 mmol), propylene oxide (PO) (43 mmol, 2.5 g), [Bmim][InCl4] (0.085 g, 0.215 mmol), NaI (0.161 g, 1.075 mmol) and tetrahydrofuran (THF) (15 mL) as a solvent were added to a 100-mL high-pressure reactor equipped with a magnetic stirrer. After performing reaction for 2 hours under a CO2 pressure of 1200 psig at 150° C., the reaction mixture was cooled to room temperature. After adding a predetermined amount (2 mL) of external standard, the solid product was separated. The separated solid product was washed 2-3 times with distilled water to remove cyclohexyl carbamate salt (CyNH3+CyNHCOO-). After further washing 2-3 times with THF, the product was completely dried in a vacuum oven. After the drying, the produced dicyclohexylurea (N,N′-dicyclohexylurea, DCU) was weighed to calculate the production yield of DCU. The conversion rate (%) of CHA and the yield of DCU were calculated according to Equation 1 and Equation 2. The residue remaining after the separation of the solid product was analyzed by gas chromatography (GC) equipped with a flame ionization detector (FID) to confirm the production of hydroxypropyl N-(cyclohexyl)carbamate (HPCC), aminoalcohol (CyNHCH2CHCH3OH, AmA) and 3-cyclohexyl-4-methyloxazolidone (CMOxz). The yields of HPCC, AmA and CMOxz were calculated using the external standard. According to the GC analysis result, the CHA conversion rate was 85.9%, the DCU yield was 47.1%, the HPCC yield was 26.7%, the CMOxz yield was 9.9%, and the AmA yield was 2.1%. Experiment was conducted under the same condition as in Example 2 while varying the promoter, i.e., the alkali metal halide. The result is shown in Table 3. As seen from Table 3, when LiI, NaI, KI, RbI or CsI was used as the promoter, there was no significant difference in HPCC and CMOxz yields, but CHA conversion rate and DCU yield were increased and the production of reaction byproducts such as AmA was suppressed. The DCU yield was the highest when NaI was used as the promoter.
1: 19.7% 2: 31.1% 3: 15.6%	With cesium chloride; 1-(n-butyl)-3-methylimidazolium tetrachloroindate In tetrahydrofuran at 150℃; for 2h;	9 Examples 14 Cyclohexylamine (CHA, also “CyNH2”) (4.26 g, 43 mmol), propylene oxide (PO) (43 mmol, 2.5 g), [Bmim][InCl4] (0.085 g, 0.215 mmol), NaI (0.161 g, 1.075 mmol) and tetrahydrofuran (THF) (15 mL) as a solvent were added to a 100-mL high-pressure reactor equipped with a magnetic stirrer. After performing reaction for 2 hours under a CO2 pressure of 1200 psig at 150° C., the reaction mixture was cooled to room temperature. After adding a predetermined amount (2 mL) of external standard, the solid product was separated. The separated solid product was washed 2-3 times with distilled water to remove cyclohexyl carbamate salt (CyNH3+CyNHCOO-). After further washing 2-3 times with THF, the product was completely dried in a vacuum oven. After the drying, the produced dicyclohexylurea (N,N′-dicyclohexylurea, DCU) was weighed to calculate the production yield of DCU. The conversion rate (%) of CHA and the yield of DCU were calculated according to Equation 1 and Equation 2. The residue remaining after the separation of the solid product was analyzed by gas chromatography (GC) equipped with a flame ionization detector (FID) to confirm the production of hydroxypropyl N-(cyclohexyl)carbamate (HPCC), aminoalcohol (CyNHCH2CHCH3OH, AmA) and 3-cyclohexyl-4-methyloxazolidone (CMOxz). The yields of HPCC, AmA and CMOxz were calculated using the external standard. According to the GC analysis result, the CHA conversion rate was 85.9%, the DCU yield was 47.1%, the HPCC yield was 26.7%, the CMOxz yield was 9.9%, and the AmA yield was 2.1%. Experiment was conducted under the same condition as in Example 2 while varying the catalyst and solvent in the absence of the promoter NaI. The result is shown in Table 1. As seen from Table 1, there was no significant difference in HPCC and CMOxz yields as compared to Example 2, but CHA conversion rate and DCU yield were lower and the production of reaction byproducts such as AmA was increased.

Reference： [1]Current Patent Assignee: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGY - US2015/133676, 2015, A1 Location in patent: Paragraph 0061; 0062; 0063
[2]Current Patent Assignee: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGY - US2015/133676, 2015, A1 Location in patent: Paragraph 0061; 0062; 0065
[3]Current Patent Assignee: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGY - US2015/133676, 2015, A1 Location in patent: Paragraph 0061; 0062; 0065

78
[ 766-93-8 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	With carbon monoxide; C₆₂H₅₂AgAu₄N₂O₄P₄⁽³⁺⁾*3F₆Sb^(1-) In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;

Reference： [1]Smirnova, Ekaterina S.; Muñoz Molina, José M.; Johnson, Alice; Bandeira, Nuno A. G.; Bo, Carles; Echavarren, Antonio M. [Angewandte Chemie - International Edition, 2016, vol. 55, # 26, p. 7487 - 7491][Angew. Chem., 2016, vol. 128, # 26, p. 7613 - 7617]

79
[ 2387-23-7 ]
[ 108-91-8 ]

Yield	Reaction Conditions	Operation in experiment
99.49%	With sodium hydroxide at 450℃; for 8h; Autoclave; Large scale;	5 Example 5 2000 kg of N, N'-dicyclohexyl urea and 4000 kg of sodium hydroxide were added to the reaction kettle, the temperature was raised to 450 ° C and the temperature was maintained at 450 ° C for 8 hours. The cyclohexanamine product was distilled out at a yield of 99.49% and a purity of 99.75%.
88%	With [Ir(H)₂(Cl)(HN{CH₂CH₂P(iPr)₂}₂)]; potassium <i>tert</i>-butylate; hydrogen In tetrahydrofuran at 130℃; for 24h; Autoclave;

Reference： [1]Current Patent Assignee: SHANDONG JINCHENG PHARMACEUTICAL & CHEMICAL CO., LTD. - CN105439870, 2016, A Location in patent: Paragraph 0025; 0026
[2]Kumar, Amit; Luk, James [European Journal of Organic Chemistry, 2021, vol. 2021, # 32, p. 4546 - 4550]

80
[ 124-38-9 ]
[ 108-91-8 ]
[ 3299-64-7 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 51.1% 2: 15.6%	With triphenylphosphine; neodymium(III) acetylacetonate In diethylene glycol dimethyl ether at 200℃; for 12h;	4 Using CO₂ N,N'-dicyclohexyl oxamalamide preparation production method Example one with the operation, the DMI of organic solvent is diethylene glycol dimethyl ether (DME), the organic amine is cyclohexylamine for butylamine replacing, lanthanum replacement is acetone neodymium tartaric acid catalyst, the molecular sieve dehydrator for triphenylporphyrin phosphorus (Ph 3 P) 13g, other conditions unchanged, when the reaction temperature is 200 °C, the reaction time is 12h time, to obtain the product N, N '-dicyclohexyl dahuricus amide. Cyclohexylamine the conversion rate of the raw material is measured to 68%. The product composition, selectivity and the yield is as shown in table 4: Table 4. Product ingredient, selectivity and the yield of Product component Selectivity (%) Yield (%) N, N '-dicyclohexyl dahuricus amide 75.2 51. 1 N, N '-dicyclohexylurea as reactants 22.9 15.6 Cyclohexyl isocyanate 1. 9 1.3

Reference： [1]Current Patent Assignee: GUANGDONG UNIVERSITY OF TECHNOLOGY - CN104610088, 2016, B Location in patent: Paragraph 0042; 0043; 0044; 0045; 0046

81
[ 108-91-8 ]
[ 80-05-7 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	With zinc(II) oxide; tetrabutyl-ammonium chloride In tetrahydrofuran at 100℃; for 7h; Autoclave; Inert atmosphere; Overall yield = 97 %;	General procedure: In a typical experiment, a 50 mL glass vial was charged withTHF (5 mL) and 1 mmol of BPA-Polycarbonate that was left to dissolve under vigorous stirring for 10 min at room temperature. Then,ZnO-NPs, Bu4NCl and nucleophile reagent were added and the vialintroduced into the autoclave, which was sealed and charged with N2 at atmospheric pressure. The autoclave was heated at 100°C forthe proper reaction time.

Reference： [1]Iannone, Francesco; Casiello, Michele; Monopoli, Antonio; Cotugno, Pietro; Sportelli, Maria Chiara; Picca, Rosaria Anna; Cioffi, Nicola; Dell'Anna, Maria M.; Nacci, Angelo [Journal of Molecular Catalysis A: Chemical, 2017, vol. 426, p. 107 - 116]

82
[ 677736-23-1 ]
[ 108-91-8 ]
C₄₃H₃₈NO₂Ru⁽¹⁺⁾*Cl^(1-) [ No CAS ]
C₄₉H₅₀N₂O₂Ru [ No CAS ]
C₄₈H₅₀N₂ORu [ No CAS ]
[ 2387-23-7 ]

Reference： [1]Dalton Transactions,2016,vol. 45,p. 11765 - 11771

83
[ 124-38-9 ]
[ 108-91-8 ]
[ 16033-71-9 ]
[ 103-00-4 ]
[ 17464-96-9 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 28.2 %Chromat. 2: 46.5% 3: 10.7 %Chromat.	Stage #1: cyclohexylamine; methyloxirane With sodium iodide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate In toluene at 20℃; for 0.0833333h; Autoclave; Stage #2: carbon dioxide In toluene at 150℃; for 2h; Autoclave;	General Procedure for the Synthesis of 1,3-Disubstituted Urea. General procedure: All the experiments related to the coupling reactionof three components (amine, CO2, and PO) were conductedin a 100-mL high-pressurized stainless steel reactorequipped with a magnetic stirrer and an electrical heater.The reactor was charged with an amine (86.1 mmol), PO(42.9 mmol), 15 mL of THF/toluene as a solvent, and therequired amount of IL used as a catalyst (0.43 mmol) with/without a promoter (2.2 mmol). The reactor was kept to homogenize the reaction mixture at 500 rpm of stirringspeed for at least 5 min at RT. (It was observed that thisstep was required for obtaining reproducible result.) Afterthat, 1.0 MPa of CO2 was purged into the reactor to deoxygenatethe reaction mixture three times. The reactor wasthen pressurized again up to 1.0 MPa of CO2 and heated upto the desired temperature with vigorous stirring. The reactorwas further pressurized up to 8.3 MPa when the temperaturereached up to 150C. Throughout the entire reactiontime, the final pressure of CO2 into the reactor (8.3 MPa)was maintained by using a gas reservoir equipped with aback-pressure regulator and a pressure transducer. At theend of the coupling reaction, the reaction mixture wasallowed to cool down and was filtered to separate out thesolid product DSU. The obtained solid product, DSU, waswashed with water to remove possible remaining carbamatesalt, and then washed with THF or toluene several times,followed by drying in a vacuum oven overnight. To the filtrate,an external standard (isooctane) was added and thesolution was analyzed by gas chromatography (GC) forquantitative analysis of other products (Oxz, AmA, andHPC). Quantitative analyses were made on an Agilent6890N gas chromatograph equipped with a flame ionizationdetector (FID) and qualitative analyses on an Agilent6890N-5975 Mass spectrometer-gas chromatograph (MSDGC)equipped with HP-5 column (30 m × 0.32 m × 0.25 μm). The dried DSU was weighed to calculate the isolatedyield (Figure 1).

Reference： [1]Son, Guang Meang; Truong, Cong Chien; Mishra, Dinesh Kumar; Mishra, Vivek; Kim, Yong Jin [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 2, p. 174 - 183]

84
[ 124-38-9 ]
[ 108-91-8 ]
[ 16033-71-9 ]
[ 103-00-4 ]
[ 96014-95-8 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 28.5% 2: 11.7 %Chromat. 3: 30.9 %Chromat.	Stage #1: cyclohexylamine; methyloxirane With sodiumtetraiodoindate(III) In toluene at 20℃; for 0.0833333h; Autoclave; Stage #2: carbon dioxide In toluene at 150℃; for 2h; Autoclave;	General Procedure for the Synthesis of 1,3-Disubstituted Urea. General procedure: All the experiments related to the coupling reactionof three components (amine, CO2, and PO) were conductedin a 100-mL high-pressurized stainless steel reactorequipped with a magnetic stirrer and an electrical heater.The reactor was charged with an amine (86.1 mmol), PO(42.9 mmol), 15 mL of THF/toluene as a solvent, and therequired amount of IL used as a catalyst (0.43 mmol) with/without a promoter (2.2 mmol). The reactor was kept to homogenize the reaction mixture at 500 rpm of stirringspeed for at least 5 min at RT. (It was observed that thisstep was required for obtaining reproducible result.) Afterthat, 1.0 MPa of CO2 was purged into the reactor to deoxygenatethe reaction mixture three times. The reactor wasthen pressurized again up to 1.0 MPa of CO2 and heated upto the desired temperature with vigorous stirring. The reactorwas further pressurized up to 8.3 MPa when the temperaturereached up to 150C. Throughout the entire reactiontime, the final pressure of CO2 into the reactor (8.3 MPa)was maintained by using a gas reservoir equipped with aback-pressure regulator and a pressure transducer. At theend of the coupling reaction, the reaction mixture wasallowed to cool down and was filtered to separate out thesolid product DSU. The obtained solid product, DSU, waswashed with water to remove possible remaining carbamatesalt, and then washed with THF or toluene several times,followed by drying in a vacuum oven overnight. To the filtrate,an external standard (isooctane) was added and thesolution was analyzed by gas chromatography (GC) forquantitative analysis of other products (Oxz, AmA, andHPC). Quantitative analyses were made on an Agilent6890N gas chromatograph equipped with a flame ionizationdetector (FID) and qualitative analyses on an Agilent6890N-5975 Mass spectrometer-gas chromatograph (MSDGC)equipped with HP-5 column (30 m × 0.32 m × 0.25 μm). The dried DSU was weighed to calculate the isolatedyield (Figure 1).

Reference： [1]Son, Guang Meang; Truong, Cong Chien; Mishra, Dinesh Kumar; Mishra, Vivek; Kim, Yong Jin [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 2, p. 174 - 183]

85
[ 124-38-9 ]
[ 108-91-8 ]
[ 16033-71-9 ]
[ 103-00-4 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 39.3% 2: 34.8 %Chromat.	Stage #1: cyclohexylamine; methyloxirane With indium (III) iodide In toluene at 20℃; for 0.0833333h; Autoclave; Stage #2: carbon dioxide In toluene at 150℃; for 2h; Autoclave;	General Procedure for the Synthesis of 1,3-Disubstituted Urea. General procedure: All the experiments related to the coupling reactionof three components (amine, CO2, and PO) were conductedin a 100-mL high-pressurized stainless steel reactorequipped with a magnetic stirrer and an electrical heater.The reactor was charged with an amine (86.1 mmol), PO(42.9 mmol), 15 mL of THF/toluene as a solvent, and therequired amount of IL used as a catalyst (0.43 mmol) with/without a promoter (2.2 mmol). The reactor was kept to homogenize the reaction mixture at 500 rpm of stirringspeed for at least 5 min at RT. (It was observed that thisstep was required for obtaining reproducible result.) Afterthat, 1.0 MPa of CO2 was purged into the reactor to deoxygenatethe reaction mixture three times. The reactor wasthen pressurized again up to 1.0 MPa of CO2 and heated upto the desired temperature with vigorous stirring. The reactorwas further pressurized up to 8.3 MPa when the temperaturereached up to 150C. Throughout the entire reactiontime, the final pressure of CO2 into the reactor (8.3 MPa)was maintained by using a gas reservoir equipped with aback-pressure regulator and a pressure transducer. At theend of the coupling reaction, the reaction mixture wasallowed to cool down and was filtered to separate out thesolid product DSU. The obtained solid product, DSU, waswashed with water to remove possible remaining carbamatesalt, and then washed with THF or toluene several times,followed by drying in a vacuum oven overnight. To the filtrate,an external standard (isooctane) was added and thesolution was analyzed by gas chromatography (GC) forquantitative analysis of other products (Oxz, AmA, andHPC). Quantitative analyses were made on an Agilent6890N gas chromatograph equipped with a flame ionizationdetector (FID) and qualitative analyses on an Agilent6890N-5975 Mass spectrometer-gas chromatograph (MSDGC)equipped with HP-5 column (30 m × 0.32 m × 0.25 μm). The dried DSU was weighed to calculate the isolatedyield (Figure 1).
1: 5.3% 2: 48.7 %Chromat.	Stage #1: cyclohexylamine; methyloxirane With indium(III) chloride In tetrahydrofuran at 20℃; for 0.0833333h; Autoclave; Stage #2: carbon dioxide In tetrahydrofuran at 150℃; for 2h; Autoclave;	General Procedure for the Synthesis of 1,3-Disubstituted Urea. General procedure: All the experiments related to the coupling reactionof three components (amine, CO2, and PO) were conductedin a 100-mL high-pressurized stainless steel reactorequipped with a magnetic stirrer and an electrical heater.The reactor was charged with an amine (86.1 mmol), PO(42.9 mmol), 15 mL of THF/toluene as a solvent, and therequired amount of IL used as a catalyst (0.43 mmol) with/without a promoter (2.2 mmol). The reactor was kept to homogenize the reaction mixture at 500 rpm of stirringspeed for at least 5 min at RT. (It was observed that thisstep was required for obtaining reproducible result.) Afterthat, 1.0 MPa of CO2 was purged into the reactor to deoxygenatethe reaction mixture three times. The reactor wasthen pressurized again up to 1.0 MPa of CO2 and heated upto the desired temperature with vigorous stirring. The reactorwas further pressurized up to 8.3 MPa when the temperaturereached up to 150C. Throughout the entire reactiontime, the final pressure of CO2 into the reactor (8.3 MPa)was maintained by using a gas reservoir equipped with aback-pressure regulator and a pressure transducer. At theend of the coupling reaction, the reaction mixture wasallowed to cool down and was filtered to separate out thesolid product DSU. The obtained solid product, DSU, waswashed with water to remove possible remaining carbamatesalt, and then washed with THF or toluene several times,followed by drying in a vacuum oven overnight. To the filtrate,an external standard (isooctane) was added and thesolution was analyzed by gas chromatography (GC) forquantitative analysis of other products (Oxz, AmA, andHPC). Quantitative analyses were made on an Agilent6890N gas chromatograph equipped with a flame ionizationdetector (FID) and qualitative analyses on an Agilent6890N-5975 Mass spectrometer-gas chromatograph (MSDGC)equipped with HP-5 column (30 m × 0.32 m × 0.25 μm). The dried DSU was weighed to calculate the isolatedyield (Figure 1).

Reference： [1]Son, Guang Meang; Truong, Cong Chien; Mishra, Dinesh Kumar; Mishra, Vivek; Kim, Yong Jin [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 2, p. 174 - 183]
[2]Son, Guang Meang; Truong, Cong Chien; Mishra, Dinesh Kumar; Mishra, Vivek; Kim, Yong Jin [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 2, p. 174 - 183]

86
[ 24424-99-5 ]
[ 108-91-8 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 20℃;	General procedure: To a solution of amine 11 (2 mmol, 1.0 equiv.) in CH2Cl2 was added successively DABCO (11.2 mg, 0.1 mmol, 0.1 equiv.) and a solution of (Boc) 2O (218 mg, 1.0 mmol, 0.5 equiv.). After the completion of the reaction as detected by TLC (30 min to 3h), the reaction mixture cooled to 0 °C, n-hexane was then added, the resulting solid was collected and further washed with cold water and diethyl ether to afford the corresponding product.

Reference： [1]Wang, Mingliang; Han, Jilai; Si, Xiaojia; Hu, Yimin; Zhu, Jidong; Sun, Xun [Tetrahedron Letters, 2018, vol. 59, # 17, p. 1614 - 1618]

87
[ 2387-23-7 ]
[ 102410-65-1 ]
C₃₆H₄₁N₃O₄ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 3026 - 3039

88
[ 29786-93-4 ]
[ 538-75-0 ]
[ 74-11-3 ]
[ 25017-08-7 ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: dicyclohexyl-carbodiimide; para-chlorobenzoic acid In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5h; Inert atmosphere;	B: General Experimental Procedure for the Synthesis of Ketone from Carboxylic Acid. Method A General procedure: To a stirred solution of carboxylic acid 1 (1 mmol) in THF (3 mL), DCC (1 mmol) was added at room temperature under N2 atmosphere. After 1 h, the mixture was cooled to -20 °C and n-BuLi (2 mmol) was added to the reaction mixture indrop wise. After 0.5 h the reaction was quenched with saturated NH4Cl solution (5 mL) at -20 C. The mixture was warmed to room temperature and extracted with ethyl acetate (10 mL ×3). The combined organic layers were washed with water (20 mL × 3), brine (20 mL) and finally dried over MgSO4. The volatiles are evaporated under reduced pressure to get a crude mass which was then purified by column chromatography on silica gel (EtOAc: petroleum ether = 1:9) to obtain pure 3.

Reference： [1]Mekonnen, Habtamu Gelaw; Jana, Samaresh [Tetrahedron Letters, 2019, vol. 60, # 20, p. 1382 - 1384]

89
[ 67531-86-6 ]
[ 2387-23-7 ]

Reference： [1]Dalton Transactions,2019,vol. 48,p. 15856 - 15868

90
[ 497-06-3 ]
[ 2387-23-7 ]
C₁₇H₂₈N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In dibutyl ether at 150℃; for 16h; Green chemistry;

Reference： [1]Adam, Rosa; Arango-Daza, Juan Camilo; Cabrero-Antonino, Jose R.; Izquierdo-Aranda, Luis; Lluna-Galán, Carles [ACS Catalysis, 2022, p. 6906 - 6922]

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P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 2387-23-7 ] {[proInfo.proName]}

Quality Control of [ 2387-23-7 ]

Related Doc. of [ 2387-23-7 ]

Product Details of [ 2387-23-7 ]

Calculated chemistry of [ 2387-23-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 2387-23-7 ]

Application In Synthesis of [ 2387-23-7 ]

[ 2387-23-7 ] Synthesis Path-Upstream 1~10

[ 2387-23-7 ] Synthesis Path-Downstream 1~90

Related Functional Groups of [ 2387-23-7 ]

Aliphatic Cyclic Hydrocarbons

Amides

Ureas

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 2387-23-7 ]