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A facile synthesis of 5(6)-(chloromethyl)benzimidazoles: Replacement of a sulfonic acid functionality by chlorine

✍ Scribed by Béla Pete; Bálint Szokol; László Toőke

Publisher: Journal of Heterocyclic Chemistry
Year: 2008
Tongue: English
Weight: 292 KB
Volume: 45
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570450208

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✦ Synopsis

Abstract

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Valuable new synthetic intermediates, 5(6)‐(chloromethyl)benzimidazoles, were prepared by the facile elimination of sulfur dioxide under the influence of thionyl chloride from benzimidazole‐5(6)‐methane‐sulfonic acids easily obtained from (3,4‐diaminophenyl)methanesulfonic acid with formic‐, or trifluoroacetic acid. Both reaction steps involved only acidic conditions, thus the synthesis of polysubstituted 5(6)‐(chloromethyl)benzimidazoles incorporating base‐sensitive substituents became possible.

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