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

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 trif...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 45; no. 2; pp. 343 - 347
Main Authors Pete, Bela, Szokol, Baliant, Toke, Laszlo
Format Journal Article
LanguageEnglish
Published MALDEN Wiley 01.03.2008
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
RECEPTOR
INHIBITORS
BENZIMIDAZOLES
5-CHLOROMETHYL-1H-INDOLE-2-CARBOXYLATES
DERIVATIVES
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Summary: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.
ISSN:0022-152X
DOI:10.1002/jhet.5570450208