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Synthesis of 2‐oxo‐3‐benzothiazolineacetyl chloride ( 7 ), 5‐chloro‐2‐oxo‐3‐benzothiazolineacetyl chloride ( 8 ) and derivatives
Author(s) -
D'Amico John J.,
Bollinger Frederick G.
Publication year - 1988
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.5570250427
Subject(s) - chemistry , thionyl chloride , acetanilide , hydrazide , chloride , amide , organic chemistry , medicinal chemistry , chloroacetyl chloride
Abstract The reaction of 2‐oxo‐3‐benzothiazolineacetic acid ( 5 ) and the 5‐chloro analogue 6 with thionyl chloride afforded the titled compounds 7 and 8 . The reaction of 7 or 8 with substituted hydrazines, amines or substituted anilines, alcohols and mercaptans furnished the hydrazides 9–14 , acetamides and acetanilides 16–21 , esters 26–30 and thiolesters 31–37 , respectively. Alternate routes for the synthesis of hydrazide 15 , acetamides and acetanilides 22–25 and thiolesters 35–36 are described. The reaction of 2‐oxo‐3(2 H )‐benzothi‐azolineacetonitrile with thioacetic acid under acidic conditions afforded 2‐oxo‐3‐benzothiazolineethanethio‐amide (38).