European Journal of Chemistry 2021, 12(2), 109-116 | doi: https://doi.org/10.5155/eurjchem.12.2.109-116.2064 | Get rights and content

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The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives


Brock Anton Stenfors (1) orcid , Felix Nyuangem Ngassa (2,*) orcid

(1) Department of Chemistry, Grand Valley State University, 1 Campus Drive, Allendale, MI 49401, USA
(2) Department of Chemistry, Grand Valley State University, 1 Campus Drive, Allendale, MI 49401, USA
(*) Corresponding Author

Received: 09 Jan 2021 | Revised: 16 Mar 2021 | Accepted: 28 Mar 2021 | Published: 30 Jun 2021 | Issue Date: June 2021

Abstract


The sulfonamide moiety is present among a variety of biologically significant compounds. A facile synthesis is necessary to produce a variety of sulfonamides with the potential to improve human health. Herein, we report a facile methodology for the synthesis of 4-methylbenzenesulfonamides, amenable to a broad range of nitrogen nucleophiles. Implementing a semi-miscible biphasic solvent system resulted in higher yields, decreased reaction times, and a simplified workup over preliminary methods. Additionally, the crystal structures of five novel sulfonamide compounds and two polymorphs, have been determined by X-ray diffraction. Results obtained through spectroscopic characterization support the successful formation of the desired 4-methylbenzenesulfonamides.


Keywords


Tosylation; Sulfa drugs; Methodology; Sulfonamides; Crystal structures; Packing polymorph

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DOI: 10.5155/eurjchem.12.2.109-116.2064

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Funding information


National Science Foundation (Grant No. MRI CHE-1725699); Grand Valley State University Chemistry Department’s Weldon Fund.

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Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Stenfors, B.; Ngassa, F. Eur. J. Chem. 2021, 12(2), 109-116. doi:10.5155/eurjchem.12.2.109-116.2064
Stenfors, B.; Ngassa, F. The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives. Eur. J. Chem. 2021, 12(2), 109-116. doi:10.5155/eurjchem.12.2.109-116.2064
Stenfors, B., & Ngassa, F. (2021). The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives. European Journal of Chemistry, 12(2), 109-116. doi:10.5155/eurjchem.12.2.109-116.2064
Stenfors, Brock, & Felix Nyuangem Ngassa. "The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives." European Journal of Chemistry [Online], 12.2 (2021): 109-116. Web. 27 Oct. 2021
Stenfors, Brock, AND Ngassa, Felix. "The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives" European Journal of Chemistry [Online], Volume 12 Number 2 (30 June 2021)

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