Organic Chemistry Portal

Abstracts

Search:

Synthesis of O-Ethyl Thioformate: A Useful Reagent for the Thioformylation of Amines

Christopher J. Borths*, Johann Chan, Brenda J. Burke, Robert D. Larsen

*Chemical Process R&D, Amgen, Inc., One Amgen Center Drive, Thousand Oaks, CA 91320, USA, Email: cborthsamgen.com

C. J. Borths, J. Chan, B. J. Burke, R. D. Larsen, Synlett, 2009, 3139-3142.

DOI: 10.1055/s-0029-1218343 (free Supporting Information)



see article for more reactions

Abstract

O-Ethyl thioformate has been synthesized from triethyl­orthoformate and hydrogen sulfide gas using sulfuric acid as Brønsted acid catalyst. The product can be isolated as a neat liquid in 83% overall yield. Both the crude and purified thiolate can be used to thioformylate various amines in good to excellent yields.

see article for more examples



Key Words

hydrogen sulfide, thioformate, thioacylation, sulfur, amines, condensation


ID: J60-Y2009-3440