Carbamates, thiolcarbamates, dithiocarbamates and thioncarbamates derived from 2‐benzothiazolinone and benzoxazolinone

Abstract

The reaction of 3‐(2‐hydroxyethyl)‐2‐benzothiazoline with methyl, phenyl isocyanate, or dimethylcarbamoyl chloride afforded the carbamates 1–4. The carbanilate 5 was prepared by the reaction of 2‐benzothiazolinone with 3‐chloropropyl‐N‐methylcarbanilate under basic conditions. The reaction of the appropriate 2‐benzothiazolinone with the appropriate 2‐chloro or 3‐chloropropyl disubstituted thiolcarbamate under basic conditions furnished the thiolcarbamates 6–14. The thiolcarbamate 15 was prepared by the reaction of sodium di‐isopropylthiolcarbamate with 3‐(chloromethyl)‐2‐benzothiazolinone. The reaction of 3‐(chloromethyl)‐2‐ben‐zothiazolinone and related compound with the appropriate sodium or triethylamine salt of disubstituted dithiocarbamate afforded the dithiocarbamate 16–22. The reaction of the appropriate xanthate with the potassium salt of bromoacetic acid and the appropriate secondary amine afforded the thionocarbamates 23–29. The thionocarbamate 30 was synthesized by the reaction of 5‐chloro‐2‐benzothiazolinone with 3‐chloropropyl diethylthionocarbamate.