Amidines. VII. : Hydrolysis and Alcoholysis of Carboxamides under Mild Conditions

概要

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Hydrolysis and alcoholysis of carboxamides derived from primary aliphatic amines were achieved under mild conditions. Amide exchange reaction between carboxamides and N^1-acyl-N^1,N^2-di (p-nitrophenyl) formamidines (1) gave N^1-acyl-N^1-alkyl-N^2-(p-nitrophenyl)formamidines (2) which were readily hydrolyzed or alcoholyzed to give N^1-alkyl-N^2-(p-nitrophenyl)formamidines (4) and carboxylic acid or its ester. Compounds 4 were hydrolyzed to give aliphatic amine and N-formyl-p-nitroaniline in the presence of acetic acid or hydrochloric acid at room temperature. For the alcoholysis of N-acyl derivatives of amino alcohols, protection of the hydroxyl substituent by an acyl group was essential because the reaction of 1 and N-acyl derivatives of amino alcohols was quite complex. Alcoholysis of N-ethyl-N, N'-ethylenebis (p-chlorobenzamide) (8a) by this method gave N-(2-aminoethyl)-N-ethyl-p-chlorobenzamide (8b). Thus, the selective alcoholysis of diacyl derivative of diamines, which contain primary and secondary amino groups, was achieved.
社団法人日本薬学会の論文
1990-07-25