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Benzothiazoline derivatives. I. Reaction of 2‐benzothiazolinethione with ethylene oxide
Author(s) -
Sohar Paul,
Denny George H.,
Babson Robert D.
Publication year - 1968
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570050605
Subject(s) - chemistry , acetic acid , ethylene oxide , ethylene , oxide , medicinal chemistry , organic chemistry , catalysis , polymer , copolymer
Treatment of 2‐benzothiazolinethione with excess ethylene oxide in acetic acid resulted in N ‐hydroxyethylation and thiono‐oxo replacement to give 3‐(2‐hydroxyethyl)‐2‐benzothiazolinone. This product was also obtained when S‐alkylthiobenzothiazoles were treated in this way. Similar treatment of the N ‐substituted compounds 3‐methyl‐2‐benzothiazolinethione and 3‐(2‐hydroxyethyl)‐2‐benzothiazolinethione gave simple thiono‐oxo replacement.