(Isocyanatomethylene)dibenzene → 1-Benzhydryl-3-(1-benzhydryl-2-oxo-pyrrolidin-3-yl)-urea

HRID 1786559

Reaction equation

HRID 1786559 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]1=[O:20].[C:21]1([CH:27]([N:34]=[C:35]=[O:36])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[CH:27]([NH:34][C:35]([NH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]1=[O:20])=[O:36])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 4250935(Isocyanatomethylene)dibenzeneHCID 575975623-Amino-1-benzhydryl-pyrrolidin-2-one

Product 1

HCID 575975821-Benzhydryl-3-(1-benzhydryl-2-oxo-pyrrolidin-3-yl)-ureaYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-1-benzhydryl-pyrrolidin-2-one (42) (0.2 g, 0.75 mmol) in dry CH2Cl2 (15 ml) was added diphenylmethyl isocyanate (0.17 mg, 0.82 mmol) dropwise under nitrogen. The resulting mixture was stirred at room temperature for two days followed by refluxing for 5 hours. Removal of solvent under reduced pressure followed by column chromatography using hexane: ethyl acetate (2:1) gave the desired product in 65% yield.

Workup

  1. temperatureby refluxing for 5 hours
  2. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-90252da0f3144d0e85fb42da01f4d4d5
Source dataset
uspto-grants-2009_03
Patent number
US07507760B2

Linked notes

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