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An Efficient Method for the Synthesis of N-Acylsulfonamides: One-pot Sulfonylation and Acylation of Primary Arylamines under Solvent-Free Conditions

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Summary.

The preparation of N-acylsulfonamides is described using primary amines, arylsulfonyl chlorides and acyl chlorides. Reaction of primary aryl amines with arylsulfonyl chlorides in the presence of NaHCO3 produced N-arylsulfonamides, which reacted in situ with benzoyl chloride furnishing the corresponding N-benzoyl-N-arylsulfonamides in 72–96% yields. Accordingly, 4-nitrobenzoyl chloride and 3,5-dinitrobenzoyl chloride were used as acylating agents. All the reactions were carried out under solvent-free conditions at room temperature and the products were isolated after simple work-up in high yields and purity.

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Authors and Affiliations

  1. Department of Chemistry, Islamic Azad University, Shahreza Branch, Isfahan, Iran

    Ahmad R. Massah, Davood Azadi, Hamid Aliyan, Ahmad R. Momeni & Hamid Javaherian Naghash

  2. Department of Chemistry, Institute for Advanced Studies in Basic Science (IASBS), Zanjan, Iran

    Foad Kazemi

Authors
  1. Ahmad R. Massah
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  2. Davood Azadi
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  3. Hamid Aliyan
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  4. Ahmad R. Momeni
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  5. Hamid Javaherian Naghash
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  6. Foad Kazemi
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Correspondence to Ahmad R. Massah.

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Massah, A., Azadi, D., Aliyan, H. et al. An Efficient Method for the Synthesis of N-Acylsulfonamides: One-pot Sulfonylation and Acylation of Primary Arylamines under Solvent-Free Conditions. Monatsh Chem 139, 233–240 (2008). https://doi.org/10.1007/s00706-007-0783-2

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  • DOI: https://doi.org/10.1007/s00706-007-0783-2

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