Methyl Diethylamidosulfite1

[21954-69-8]  · C5H13NO2S  · Methyl Diethylamidosulfite  · (MW 151.26)

(conversion of carboxylic acids to N,N-diethylamides2)

Physical Data: bp 73-74 °C/10 mmHg.

Solubility: sol diethyl ether.

Form Supplied in: clear oil.

Analysis of Reagent Purity: titration with iodine.

Preparative Method: reaction of diethylamine and chlorosulfurous acid in diethyl ether.1,2

Purification: vacuum distillation.2

Handling, Storage, and Precautions: prolonged heating at atmospheric pressure causes decomposition with evolution of sulfur dioxide.

This reagent reacts with primary and secondary carboxylic acids in the presence of pyridine to give N,N-diethylamides (eq 1). The reaction is typically run at rt and requires a long reaction time (several days). In general, tertiary acids and a-amino carboxylic acids do not react.2,3

1. (a) Zinner, G. CB 1958, 91, 966. (b) Voss, M.; Blanke, E. LA 1931, 485, 258.
2. Takei, H.; Shimizu, H.; Hizo, M.; Mukaiyama, T. BCJ 1968, 41, 1925.
3. Becker, H. G. O.; Funk, K. F. JPR 1961, 14, 55.

Brian A. Roden

Abbott Laboratories, North Chicago, IL, USA

Copyright 1995-2000 by John Wiley & Sons, Ltd. All rights reserved.