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A modified synthesis of 4‐chloromethylthiazoles
Author(s) -
Marzoni Gifford
Publication year - 1986
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.5570230253
Subject(s) - chemistry , thionyl chloride , phosphorus pentachloride , sulfuryl chloride , thioamide , phosphorus trichloride , phosphoryl chloride , chloride , aryl , organic chemistry , alkyl , medicinal chemistry , bicarbonate , solvent
Abstract A two‐reaction synthesis of 2‐substituted‐4‐chloromethylthiazoles from thioamides and 1,3‐dichloroacetone is reported. The first step, cyclization to a 2‐substituted‐4‐chloromethyl‐4‐hydroxythiazoline is carried out in the presence of bicarbonate in an aprotic solvent. Dehydration of this intermediate to a 2‐substituted‐4‐chloromethylthiazole is accomplished by reaction with thionyl chloride, sulfuryl chloride, phosphoryl chloride, phosphorus trichloride or phosphorus pentachloride. Substituents on the thioamide, such as amino, alkyl, or aryl, are shown not to affect the success of the reaction. As a trend, alkylthioamides give slightly better yields of 4‐chloromethylthiazoles than do arylthioamides. The yields of 4‐chloromethylthiazoles prepared using this procedure are comparable to the yields obtained using acid catalyzed procedures.