Facile Synthesis of N-Substituted Amides from Alcohols and Amides

Iku Okada; Kazuhiro Chiba; Yoshikazu Kitano

doi:10.1055/s-0032-1318477

Synthesis, Table of Contents

Synthesis 2013; 45(8): 1069-1075
DOI: 10.1055/s-0032-1318477

paper

Facile Synthesis of N-Substituted Amides from Alcohols and Amides

Iku Okada

Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu-shi, Tokyo 183-8509, Japan Fax: +81(42)3675700 Email: kitayo@cc.tuat.ac.jp

,

Kazuhiro Chiba

Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu-shi, Tokyo 183-8509, Japan Fax: +81(42)3675700 Email: kitayo@cc.tuat.ac.jp

,

Yoshikazu Kitano*

Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu-shi, Tokyo 183-8509, Japan Fax: +81(42)3675700 Email: kitayo@cc.tuat.ac.jp

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Abstract

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Abstract

A facile and versatile method for preparing N-substituted amides from alcohols and amides using a Brønsted acid and an alkali metal halide has been developed. Treatment of tertiary alcohols and amides in the presence of an alkali metal halide or methanesulfonic acid in trifluoroacetic acid at elevated temperature afforded the corresponding N-substituted amides in moderate to high yields. Tertiary alcohols with various functional groups such as ether, ester, imide, carbamate, and halogen groups were tolerated under these conditions. This method can be used for the efficient and practical synthesis of various N-substituted formamides without the use of unmanageable cyano compounds.

Key words

amides - alcohols - Brønsted acids - alkali metal halides - nucleophilic substitution

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References

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