Tetrahedron

Novel and efficient method for esterification, amidation between carboxylic acids and equimolar amounts of alcohols, and amines utilizing Me 2 NSO 2 Cl and N, N- …

K Wakasugi, A Nakamura, A Iida, Y Nishii, N Nakatani…

Index: Wakasugi, Kazunori; Nakamura, Atsushi; Iida, Akira; Nishii, Yoshinori; Nakatani, Nobuji; Fukushima, Shoji; Tanabe, Yoo Tetrahedron, 2003 , vol. 59, # 28 p. 5337 - 5345

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Citation Number: 48

Abstract

Various carboxylic esters or amides were prepared in good to excellent yield between carboxylic acids and equimolar amounts of alcohols or amines under very mild conditions (0– 45° C; within 3 h) using dimethylsulfamoyl chloride (Me2NSO2Cl; 1) combined with N, N- dimethylamines (Me2NR: 2a; R= Me, 2b; R= Bu). The choice of the sulfamoyl chloride and the amine is crucial for the reaction; that is, sterically uncrowded amines accelerated the ...