Derivatives of 3‐(2‐hydroxyethyl)2‐benzothiazolinone and related compounds

Abstract

The reaction of the appropriate 2‐benzothiazolinone with 2‐chloroethanol or 3‐chloropropanol under basic conditions afforded 3‐(2‐hydroxyethyl or 3‐hydroxypropyl)‐2‐benzothiazolinone and related compounds 1–7. The reaction of the alcohols 1,4, 5 or 7 with potassium hydroxide and excess carbon disulfide furnished the potassium salts of xanthic acid 8–11 which upon oxidation gave the disulfides 12–15. Esters of xanthic acid 16–23 were prepared by the reaction of 8 or 11 with various halogen compounds. Esters of acetic acid 24–28 were prepared by the reaction of the appropriate 2‐benzothiazolinone with 2‐bromoethyl acetate under basic conditions. Esterification of 1 with various acids afforded the esters 25, 29–32.