Amidation of Alcohols with Nitriles under Solvent-free Conditions Using Molecular Iodine as a Catalyst

Yoshio Kasashima; Atsushi Uzawa; Kahoko Hashimoto; Yu Yokoyama; Takashi Mino; Masami Sakamoto; Tsutomu Fujita

doi:10.5650/jos.59.607

Chemistry and Organic Synthesis

Amidation of Alcohols with Nitriles under Solvent-free Conditions Using Molecular Iodine as a Catalyst

Yoshio Kasashima, Atsushi Uzawa, Kahoko Hashimoto, Yu Yokoyama, Takashi Mino, Masami Sakamoto, Tsutomu Fujita

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Keywords: iodine, solvent-free, amidation, borneol

JOURNAL FREE ACCESS

2010 Volume 59 Issue 11 Pages 607-613

DOI https://doi.org/10.5650/jos.59.607

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Abstract

The reactions of alcohols with nitriles under solvent-free conditions, using molecular iodine as a catalyst, were investigated. The reaction of 1-phenylethanol with propanenitrile produced the amide N-(1-phenylethyl)propanamide, by dehydration and tautomerization, in 71% yield, under the following conditions: temperature=90°C, alcohol:iodine molar ratio=1:0.2, alcohol:nitrile molar ratio=1:5, and reaction time=5 h. The amidation reactivity depended on the stability of the cationic intermediate formed from the alcohol. The reaction of (–)-borneol with benzonitrile produced a racemic amide in 83% yield.

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