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

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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.

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Key Words

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

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ID: J60-Y2009-3440