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Chemistry
Heterocyclic Building Blocks
Indoles
5-((1H-Indol-3-yl)methyl)imidazolidine-2,4-dione
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Indoles
Imidazolidines Amides

[ CAS No. 21753-16-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 21753-16-2
Chemical Structure| 21753-16-2
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Quality Control of [ 21753-16-2 ]

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Product Details of [ 21753-16-2 ]

CAS No. :21753-16-2 MDL No. :MFCD01850992
Formula : C12H11N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 229.24 Pubchem ID :-
Synonyms :

Safety of [ 21753-16-2 ]

Signal Word: Class:
Precautionary Statements: UN#:
Hazard Statements: Packing Group:

Application In Synthesis of [ 21753-16-2 ]

* 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.

  • Downstream synthetic route of [ 21753-16-2 ]

[ 21753-16-2 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 117490-34-3 ]
  • [ 21753-16-2 ]
Reference： [1]Journal of the Chemical Society,1944,p. 629,631
[2]Journal of the Chemical Society,1944,p. 629,631
  • 2
  • [ 21753-16-2 ]
  • [ 105-36-2 ]
  • [ 109498-12-6 ]
Reference： [1]Monatshefte fur Chemie,1956,vol. 87,p. 425,434
  • 3
  • [ 21753-16-2 ]
  • [ 73-22-3 ]
Reference： [1]Agricultural and Biological Chemistry,1987,vol. 51,p. 363 - 370
[2]Bulletin de la Societe Chimique de France,1980,vol. 2,p. 91 - 95
  • 6
  • 5-<indolyl-(3)-methylene>-hydantoin [ No CAS ]
  • [ 21753-16-2 ]
Reference： [1]Chemische Berichte,1922,vol. 55,p. 3870
    Chemische Berichte,1930,vol. 63,p. 2239
  • 7
  • [ 21753-16-2 ]
  • aq. barium hydroxide solution [ No CAS ]
  • [ 54-12-6 ]
Reference： [1]Chemische Berichte,1922,vol. 55,p. 3870
    Chemische Berichte,1930,vol. 63,p. 2239
  • 8
  • [ 1118-02-1 ]
  • [ 7303-49-3 ]
  • [ 21753-16-2 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5039 - 5044
  • 9
  • 5-(1H-indol-3-ylmethyl)-imidazolidine-2,4-dione potassium salt [ No CAS ]
  • [ 2290-65-5 ]
  • [ 21753-16-2 ]
YieldReaction ConditionsOperation in experiment
93% With triethylamine; In dichloromethane; for 5.0h; To a solution of L-tryptophan methyl ester hydrochloride (0.500 mg, 0.002 mol.) in dichloromethane (10 mL) was added triethyl amine (3.0 mL) followed by trimethylsilylisocyanate (2.300 gm, 0.02 mol.). The reaction mixture was stirred at room temperature for 24 hr and then concentrated. The residue obtained was dissolved in AcOH (5 mL) and refluxed for 5 hr. The reaction mixture was extracted in ethyl acetate, washed with water, dried and concentrated. The residue was dissolved in EtOH and treated with KOH, and stirred for 30 min. Then the reaction was concentrated and dried under vacuum to give 5-(1H-indol-3-ylmethyl)-imidazolidine-2,4-dione potassium salt (245 mg, 46%). This solid (50 mg, 0.18 mg) was acidified with dilute HCl at 0 C. The residue was extracted in ethyl acetate, and concentrated. The solid obtained after concentration was dried under vacuum to give 893-19 (42 mg, 93%)
Reference： [1]Patent: US2005/119260,2005,A1 .Location in patent: Page/Page column 35
  • 10
  • C2 H5 OH [ No CAS ]
  • NaOC2 H5 [ No CAS ]
  • [ 21753-16-2 ]
  • [ 7732-18-5 ]
  • [ 5472-49-1 ]
  • 5-(Indol-3-ylmethyl)-3-(3-piperidylpropyl)hydantoin [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; EXAMPLE 20 5-(Indol-3-ylmethyl)-3-(3-piperidylpropyl)hydantoin A mixture of 5-(indol-3-ylmethyl)hydantoin (10 g, 0.043 mole), N-(3-chloropropyl)piperidine hydrochloride (8.6 g, 0.043 mole), NaOC2 H5 (0.086 mole), 350 ml of anhydrous C2 H5 OH and 100 ml DMF was heated to reflux with stirring for 6 hours and poured into 1.5 l of H2 O. The solid was collected and recrystallized from aqueous methanol, yield 11.7 g, mp 185. ANALYSIS-- Calculated for C20 H26 N4 O2: C, 67.78; H, 7.39; N, 15.81. Found: C, 67.45; H, 7.32; N, 15.64.
Reference： [1]Patent: US4110536,1978,A
  • 11
  • [ 21753-16-2 ]
  • [ 75-64-9 ]
  • [ 106-89-8 ]
  • [ 69244-12-8 ]
YieldReaction ConditionsOperation in experiment
In C2 H5 OH; NaOC2 H5; EXAMPLE 19 3-(3-t-Butylamino-2-hydroxypropyl)-5-(indol-3-ylmethyl)hydantoin A mixture of 5-(indol-3-ylmethyl)hydantoin (11.5 g, 0.05 mole) in NaOC2 H5 (0.05 mole) and 300 ml of anhydrous C2 H5 OH was heated to reflux and 20 g of epichlorohydrin were added. The mixture was heated to reflux for 7 hours, filtered and concentrated in vacuo to an oil. The concentrate and t-butylamine (10 ml) in 100 ml of anhydrous C2 H5 OH were heated to reflux for 3 hours and concentrated in vacuo. The free base crystallized in ether and was recrystallized from 2-propanol-petroleum ether.
Reference： [1]Patent: US4110536,1978,A
  • 12
  • NaOC2 H5 [ No CAS ]
  • [ 15037-34-0 ]
  • [ 21753-16-2 ]
  • [ 69243-99-8 ]
YieldReaction ConditionsOperation in experiment
In C2 H5 OH; N,N-dimethyl-formamide; EXAMPLE 9 5-(Indol-3-ylmethyl)-3-[3-(4-phenyl-1-piperidyl)propyl]hydantoin A mixture of 5-(indol-3-ylmethyl)hydantoin (6.4 g, 0.028 mole), 1-(3-chloropropyl)-4-phenylpiperidine (6.6 g, 0.028 mole) and 200 ml of DMF in 200 ml of anhydrous C2 H5 OH and 0.028 mole of NaOC2 H5 was heated under reflux with stirring for 10 hours. The mixture was filtered and the filtrate was diluted with H2 O. The solid was collected and twice recrystallized from aqueous C2 H5 OH, yield 2.0 g, mp 179-80. ANALYSIS-- Calculated for C26 H30 N4 O2: C, 72.53; H, 7.02; N, 13.01. Found: C, 72.02; H, 7.06; N, 12.75.
Reference： [1]Patent: US4110536,1978,A
  • 13
  • C2 H5 OH [ No CAS ]
  • NaOC2 H5 [ No CAS ]
  • [ 21753-16-2 ]
  • [ 4535-85-7 ]
  • [ 69244-09-3 ]
YieldReaction ConditionsOperation in experiment
In chloroform; EXAMPLE 16 3-(3-Diethylaminopropyl)-5-(indol-3-ylmethyl)hydantoin A mixture of 5-(indol-3-ylmethyl)hydantoin (10 g, 0.04 mole), 3-chloro-N,N-diethylpropylamine hydrochloride (8.2 g, 0.04 mole), NaOC2 H5 (0.08 mole) and 500 ml of anhydrous C2 H5 OH was heated to reflux with stirring for 20 hours. The mixture was filtered and concentrated to dryness. The concentrate was dissolved in CHCl3, filtered and concentrated. The concentrate was crystallized and recrystallized from benzene-petroleum ether. The solid was again recrystallized from xylene and the solvated solid was dried in vacuum, yield 2.5 g, mp 90. ANALYSIS-- Calculated for C19 H26 N4 O2: C, 66.64; H, 7.65; N, 16.36. Found: C, 66.04; H, 7.62; N, 15.99.
Reference： [1]Patent: US4110536,1978,A
  • 14
  • NaOC2 H5 [ No CAS ]
  • 1-(3-chloropropyl)-morpholine [ No CAS ]
  • [ 21753-16-2 ]
  • [ 69243-93-2 ]
YieldReaction ConditionsOperation in experiment
In C2 H5 OH; EXAMPLE 5 5-[(Indol-3-yl)methyl]-3-(3-morpholinopropyl)hydantoin 5-[(Indol-3-yl)methyl]hydantoin (5 g; 0.022 mole) was added to NaOC2 H5 (0.022 mole) in 300 ml of anhydrous C2 H5 OH. The first mixture was heated to reflux, and 1-(3-chloropropyl)-morpholine (3.5 g, 0.022 mole) was added. The mixture was heated for 6 hours and then diluted with H2 O. The solid was collected and recrystallized from 2-propanol-petroleum ether, yield 3 g, mp 158-60. ANALYSIS-- Calculated for C19 H25 ClN4 O3: C, 59.09; H, 6.41; N, 14.26. Found: C, 57.50; H, 6.46; N, 13.96.
Reference： [1]Patent: US4110536,1978,A

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