Collect. Czech. Chem. Commun. 2000, 65, 621-630

A Facile Synthesis of Carboxamides by Dehydration Condensation Between Free Carboxylic Acids and Amines Using O,O'-Di(2-pyridyl) Thiocarbonate as a Coupling Reagent

Isamu Shiina, Katsuyuki Saitoh, Masakazu Nakano, Yoshihito Suenaga and Teruaki Mukaiyama*

Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan


Carboxamides are prepared in high yields by dehydration condensation between nearly equimolar amounts of free carboxylic acids and amines both of which involve secondary or tertiary alkyl substituted ones with O,O'-di(2-pyridyl) thiocarbonate, a coupling reagent, in the presence of a catalytic amount of 4-(dimethylamino)pyridine.

Keywords: O,O'-Di(2-pyridyl) thiocarbonate; 4-(Dimethylamino)pyridine; 2-Pyridyl esters; Dehydration condensation; Carboxamides; Amides.

References: 20 live references.