Amide Synthesis from Esters with Nitriles under Solvent-free Conditions Using Molecular Iodine as a Catalyst

被引：10

作者：

Hanzawa, Yohko ^{[1
]}

Kasashima, Yoshio ^{[1
]}

Tomono, Kazuki ^{[2
]}

Mino, Takashi ^{[2
]}

Sakamoto, Masami ^{[2
]}

Fujita, Tsutomu ^{[2
]}

机构：

[1] Chiba Inst Technol, Educ Ctr, Fac Engn, Narashino, Chiba 2750023, Japan

[2] Chiba Univ, Grad Sch Engn, Inage Ku, Chiba 2638522, Japan

来源：

JOURNAL OF OLEO SCIENCE | 2012年 / 61卷 / 07期

关键词：

iodine; solvent-free; Ritter reaction; borneol; ONE-POT SYNTHESIS; TERT-BUTYL AMIDES; EFFICIENT; ALCOHOLS; AMIDATION;

D O I：

10.5650/jos.61.393

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The reaction of esters with nitriles, using iodine as a catalyst under solvent-free conditions, was investigated. For example, 1-phenylethyl acetate reacted with benzonitrile in the presence of iodine to afford the amide, N-(1-phenylethyl)benzamide. Addition of water was effective in promoting amidation. The most suitable conditions were investigated, and determined as follows: temperature = 80 degrees C, molar ratio of nitrile:alcohol:iodine:water = 1:3:0.2:1.0, and reaction time = 18 h. The amidation reactivity depended on the stability of the cationic intermediate formed from the ester. Only the reaction of 2-phenylpropan-2-yl acetate with benzonitrile gave no amide compound; rather, the cyclic compound, 1,1,3-trimethyl-3-phenyl-2,3-dihydro-1H-indene was obtained in 90% yield. The reaction of (-)-bornyl acetate with benzonitrile produced the racemic amide compound, (+/-)-exo-N-isobornylbenzamide, in 82% yield.

引用

页码：393 / 399

页数：7

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