Some chemistry of 4,5-dichloro-1,2,3-dithiazolium chloride and its derivatives

Abstract

4,5-Dichloro-1,2,3-dithiazolium chloride 1 reacts with fluoroanilines (see Table 1) to give the iminodithiazoles 5 in very high yield. Thermolysis of the latter gave the corresponding 2-cyanobenzothiazoles 6 together, in some cases, with the cyanoimidoyl chlorides 7. This reaction sequence provides modest yields of 2-cyanobenzothiazoles from the corresponding aniline, in two steps. Treatment of the iminodithiazoles with m-chloroperbenzoic acid in dichloromethane at or below room temperature opened the heterocyclic ring to give the N-arylcyanothioformamides (e.g.8→10), except for the p-nitrophenyl compound which gave p-nitrophenyl isothiocyanate 14 in high yield.