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Synthesis 2009(23): 3983-3988  
DOI: 10.1055/s-0029-1217020
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of Sulfonamides from Primary and Secondary Amine Derived Sulfonate Salts Using Cyanuric Chloride

Mohammad Navid Soltani Rad*a, Ali Khalafi-Nezhad*b, Zeinab Asrarib, Somayeh Behrouzb, Zohreh Aminia, Marzieh Behrouzb
Department of Chemistry, Faculty of Basic Sciences, Shiraz University of Technology, Shiraz 71555-313, Iran
Fax: +98(711)7354523; e-Mail: soltani@sutech.ac.ir; e-Mail: nsoltanirad@gmail.com;
Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
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Received 9 July 2009
Publikationsdatum:
23. September 2009 (online)

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Abstract

A convenient, mild and efficient one-pot synthesis of new sulfonamides is described. The reaction of primary or secondary amine derived sulfonate salts in the presence of cyanuric chloride, triethylamine as base, and anhydrous acetonitrile as solvent at room temperature gives the corresponding sulfonamides in good to excellent yields.

Key words

one-pot reaction - sulfonamides - amine-sulfonate salt - cyanuric chloride - triethylamine

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The ab initio (6-31G) quantum mechanic calculations were run using Gaussian 98, version 9.2. The semi-empirical Austin Model 1 (AM1) and Parameterized Model 3 (PM3) calculations were run on MOPAC in CS Chem 3D Ultra 8 (2004 Cambridge Soft) and Hyperchem (Hypercube Inc., version 7). The heat of formation (ΔHf) is a parameter used to estimate the stability of molecules in comparison with other related isomers or molecules. The molecule with the lowest ΔHf value is the most stable.

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The amine-sulfonate salts are prepared as follows: to a soln of amine (1 equiv) in a minimum amount of H2O-MeOH (60:40) was added the sulfonic acid (1 equiv). The reaction was stirred at r.t. for 15 min and the reaction was judged to be complete when pH paper indicated that the soln was neutral. The soln was evaporated under vacuum and the remaining solid was crystallized from hot MeOH. The crystals were dried in a vacuum oven for 24 h at 50 ˚C and then stored in a desiccator.