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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 12
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Original Articles

Convenient One‐Pot Synthesis of Sulfonamides from Thiols using Trichloroisocyanuric Acid

Jason D. Bonk 3M Pharmaceuticals, Chemistry Department, St. Paul, Minnesota, USACorrespondence[email protected]
,
David T. Amos 3M Pharmaceuticals, Chemistry Department, St. Paul, Minnesota, USA
&
Sarah J. Olson 3M Pharmaceuticals, Chemistry Department, St. Paul, Minnesota, USA
Pages 2039-2050 | Received 27 Oct 2006, Published online: 22 Jun 2007
 
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Abstract

A convenient synthesis of sulfonamides from thiols is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with trichloroisocyanuric acid (TCCA), benzyltrimethylammonium chloride and water (2.5 equiv). The sulfonyl chlorides are then further allowed to react with excess amine in the same reaction vessel. Triethylamine can be optionally added as acid scavenger.

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