ON INTERACTION OF 2-AMINOBENZOTHIAZOLES WITH HALOHYDRINS

Abstract

Interaction of 2-aminobenzothiazoles with ethylene chlorohydrin on boiling leads mainly to formation of the corresponding 3-(β-chloroethyl)benzothiazolin-2-ones. Reducing the reaction temperature increases the fraction of 2-imino-(3-β-hydroxyethyl)benzothiazolines. In both instances formation of bis[3-(β-hydroxyethyl)benzothiazol-2-ylidene]ammonium chlorides is observed. The reaction of 2-aminobenzo-thiazole with propylene bromohydrin gives only the corresponding amino alcohols. The anomalous products from the reaction of β-chloroethyl derivatives of benzothiazolinones result from a dominating side reaction of the starting 2-aminobenzothiazoles with the ethylene chlorohydrin thermolysis products that are formed on boiling.

Author: R. F. Ambartsumova.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (7), pp 860-865

http://link.springer.com/article/10.1007/BF02252113