Amidation of alcohols with nitriles under solvent-free conditions using molecular iodine as a catalyst.
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.
Kasashima
Yoshio
Y
Education Center, Faculty of Engineering, Chiba Institute of Technology, Chiba, Japan. yoshio.kasashima@it-chiba.ac.jp
Uzawa
Atsushi
A
Hashimoto
Kahoko
K
Yokoyama
Yu
Y
Mino
Takashi
T
Sakamoto
Masami
M
Fujita
Tsutomu
T
D000577:Amides / Q000138:chemical synthesis*; D001592:Benzyl Alcohols / Q000737:chemistry*; D001892:Camphanes / Q000737:chemistry; D002384:Catalysis; D003681:Dehydration; D007455:Iodine; D009570:Nitriles / Q000737:chemistry*; D055601:Organic Chemistry Phenomena; D012997:Solvents; D013237:Stereoisomerism; D013696:Temperature
D000577:Amides; D001592:Benzyl Alcohols; D001892:Camphanes; D009570:Nitriles; D012997:Solvents; D007455:Iodine; C014356:benzonitrile; C002017:methylphenyl carbinol; C022871:isoborneol