Reaction #5727

Reaction equation

2,6-dichlorobenzoylisocyanate

p-chloroaniline-acetonitrile

→

N-(2,6-dichlorobenzoyl)-N'-(cyanomethyl)-N'-(p-chlorophenyl)-urea

Yield 80.0%

Solvents

benzene

Conditions

Workup

1. 1
   OtherAfter some time a substance crystallizes out
2. 2
   Washwashed with benzene
3. 3
   OtherAfter drying the weight
4. 4
   Otherbeing 185° C. with spontaneous decomposition on the Kofler
5. 5
   Temperatureheating bench
6. 6
   Otherit may be recrystallized from 250 ml of benzene with a yield of 80%

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%.

Source