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Acylation of Nitrogen Heterocycles under the Conditions of the Schotten‐Baumann Reaction I: Benzimidazoles
Author(s) -
BenIshai D.,
Babad E.,
Bernstein Z.
Publication year - 1968
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.196800074
Subject(s) - chemistry , acylation , benzimidazole , imidazole , chloride , benzoyl chloride , organic chemistry , medicinal chemistry , acetyl chloride , aqueous solution , benzyl chloride , ring (chemistry) , acyl chloride , nitrogen , catalysis
The acylation of N‐monosubstituted benzimidazoles with various acid chlorides in ethyl acetate — aqueous bicarbonate mixture was investigated. The reaction, which leads to the fission of the imidazole ring, was found to be strongly dependent on the substitution on both the benzimidazole and the acid chloride used. Electron withdrawing groups in the benzimidazoles were found to facilitate the reaction. Carbobenzoxy chloride and ort ho substituted benzoyl chloride gave the highest yields of the fission products. The carbobenzoxylation and benzoylation of unsubstituted, 2‐monosubstituted and 1,2‐disubstituted benzimidazoles were also investigated.