N-(2,6-Dichlorophenyl)thiourea → 1,3-Dichloro-2-isothiocyanatobenzene

Participants

Reaction Steps

A solution of 156.9 g. of 1-(2,6-dichlorophenyl)thiourea in 1 1. of chlorobenzene was refluxed for 20 hours and concentrated. The resulting oil was triturated with 1 1. of hot hexane which was filtered. On cooling overnight, 52 g. (36%) of 2,6-dichlorophenylisothiocyanate, m.p. 41°-42° separated. Concentration of the filtrate gave an additional 64.2 g. (44%), m.p. 41°-43° in two crops. Recrystallization of a sample from hexane gave the analytical sample, m.p. 41°-42°.

Provenance & Evidence