Benzene, 1-chloro-3-isocyanato- → N-(3-Chlorophenyl)-N'-(1,3-dimethyl-4-oxoimidazolidin-2-ylidene)urea

HRID 2398580

Reaction equation

HRID 2398580 reaction equation
[CH3:1][N:2]1[CH2:6][C:5](=[O:7])[N:4]([CH3:8])[C:3]1=[NH:9].[Cl:10][C:11]1[CH:12]=[C:13]([N:17]=[C:18]=[O:19])[CH:14]=[CH:15][CH:16]=1>O1CCCC1>[Cl:10][C:11]1[CH:12]=[C:13]([NH:17][C:18]([N:9]=[C:3]2[N:4]([CH3:8])[C:5](=[O:7])[CH2:6][N:2]2[CH3:1])=[O:19])[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 140604272-Imino-1,3-dimethylimidazolidin-4-one

Product 1

HCID 54371002N-(3-Chlorophenyl)-N'-(1,3-dimethyl-4-oxoimidazolidin-2-ylidene)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6.35 g (0.050 mole) of 1,3-dimethyl-2-iminoimidazolidin-4-one, 7.85 g (0.050 mole) of 3-chlorophenylisocyanate and 75 ml of dry tetrahydrofuran is stirred at room temperature for four hours. The solution is evaporated in vacuo and the residue is crystallized from acetonitrile. Two recrystallizations from acetonitrile - ether gives pure product, 1-(3-chlorophenyl)-3-(1,3-dimethyl-4-oxo-2-imidazolidinylidene)urea, m.p. 134°-137° C.

Workup

  1. customThe solution is evaporated in vacuo
  2. customthe residue is crystallized from acetonitrile
  3. customTwo recrystallizations from acetonitrile - ether

Sources & evidence

ORD record
ord-fc23527607c04377a272ee457c95ad26
Source dataset
uspto-grants-1977_05
Patent number
US04025517

Linked notes

Loading…