Chemoselective Alcoholysis of Acylureas

Keiki Kishikawa; Hiroshi Eida; Shigeo Kohmoto; Makoto Yamamoto; Kazutoshi Yamada

doi:10.1055/s-1994-25432

Synthesis 1994; 1994(2): 173-175
DOI: 10.1055/s-1994-25432

short paper

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Chemoselective Alcoholysis of Acylureas

Keiki Kishikawa^* , Hiroshi Eida, Shigeo Kohmoto, Makoto Yamamoto, Kazutoshi Yamada

^*Department of Materials Science, Faculty of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263, Japan

Abstract

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Two methods for the chemoselective alcoholysis of acylureas were developed to generate esters and amides, respectively. In alcoholysis using sodium methoxide in methanol, methoxide attacked the acyl carbonyl to give the corresponding methyl ester. While in alcoholysis using lithium benzyloxide in diethyl ether, benzyloxide attacked the urea carbonyl to give the amide. The chemoselectivity originates in the different chelating abilities of the metals and the polarity of the solvents.

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