Reaction of 2-chloroethyl isothiocyanate with N-phenylethyleneimine and ethylene sulfide
The reaction of 2-chloroethyl isothiocyante with N-phenylethyleneimine in the presence of triethylamine gives 2-(2-chloroethyl)imino-3-phenyl-1,3-thiazolidine. A mixture (1∶2) of 2-(2-chloroethyl)imino-3-phenyl-l,3-thiazolidine and 7-phenyl-2,3,5,6-tetrahydroimidazo-[2,1-b]thiazolinium chloride is obtained in the absence of a catalyst. The reaction of 2-chloroethyl isothiocyanate with ethylene sulfide in the presence of triethylamine gives 2,3,5,6-tetrahydrothiazolo[2,3-b]thiazolinium chloride, while the reaction with tetraethyl-ammonium bromide gives 2-ethyleneiminium-l,3-dithiolane chloride.