[(4-Chlorophenyl)amino]acetonitrile → N-(2,6-dichlorobenzoyl)-N'-(cyanomethyl)-N'-(p-chlorophenyl)-urea

HRID 5631Notes

Reaction equation

HRID 5631 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[Cl:14][C:15]1[CH:24]=[CH:23][C:18]([NH:19][CH2:20][C:21]#[N:22])=[CH:17][CH:16]=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:3]=1[C:4]([NH:6][C:7]([N:19]([CH2:20][C:21]#[N:22])[C:18]1[CH:17]=[CH:16][C:15]([Cl:14])=[CH:24][CH:23]=1)=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 90639[(4-Chlorophenyl)amino]acetonitrileHCID 129127392,6-Dichlorobenzoyl isocyanate

Product 1

HCID 19006392N-(2,6-dichlorobenzoyl)-N'-(cyanomethyl)-N'-(p-chlorophenyl)-ureaYield 80%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

16.0 g of 2,6-dichlorobenzoylisocyanate are added in small portions to a solution of 11.66 g of p-chloroaniline-acetonitrile in 100 ml of dry benzene with moderate cooling. After some time a substance crystallizes out, which after about 12 hours is drawn off and washed with benzene. After drying the weight is 25.25 g, i.e. 93.7% the melting point being 185° C. with spontaneous decomposition on the Kofler heating bench. Thin-layer chromatography (solvent either ethylacetate or chloroform) shows that the substance is pure, however, if desired, it may be recrystallized from 250 ml of benzene with a yield of 80%.

Workup

  1. customAfter some time a substance crystallizes out
  2. washwashed with benzene
  3. customAfter drying the weight
  4. custombeing 185° C. with spontaneous decomposition on the Kofler
  5. temperatureheating bench
  6. customit may be recrystallized from 250 ml of benzene with a yield of 80%

Sources & evidence

ORD record
ord-4b7507acb22e4bf8a1321040f57cb521
Source dataset
uspto-grants-1993_09
Patent number
US05245071

Reaction notes

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