Water → HCID 21483060, compound

Participants

Reaction Steps

2-Chloroethyl chloroformate (14.3 g; 0.10 mole) was added dropwise to a stirred suspension of potassium thiocyanate (11.7 g; 0.12 mole) in dry acetonitrile (100 ml). The temperature of the reaction mixture rose spontaneously to 40° C. and stirring was continued for two hours at 30° C. to 40° C. The reaction mixture was then filtered and the clear filtrate was added dropwise during fifteen minutes to a stirred suspension of o-phenylenediamine (10.8 g; 0.10 mole) in dry acetonitrile (50 ml), the temperature during the addition being maintained between 15°C. and 20° C. by external cooling. When the addition was complete the reaction mixture was stirred at 30° to 40° C. for two hours, and poured into water (1litre). The crude solid which separated was filtered off, washed with water and crystallised from methanol to give 1-(2-chloroethoxycarbonyl)-3-(2-aminophenyl)thiourea (14.9 g), m.p. 173°-174°C. (with decomposition).

Provenance & Evidence