European Journal of Chemistry

The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives

Article Sidebar

PDF CIF FILE CIF FILE CIF FILE CIF FILE CIF FILE CIF FILE CIF FILE
Published: Jun 30, 2021
DOI: https://doi.org/10.5155/eurjchem.12.2.109-116.2064
Keywords:
Tosylation, Sulfa drugs, Methodology, Sulfonamides, Crystal structures, Packing polymorph
Section
Research Article
Issue
Vol. 12 No. 2 (2021): June 2021
Dates
Received 2021-01-09
Accepted 2021-03-28
Published 2021-06-30
Crossmark


Main Article Content

Brock Anton Stenfors
Department of Chemistry, Grand Valley State University, 1 Campus Drive, Allendale, MI 49401, USA
https://orcid.org/0000-0001-8760-5878
Felix Nyuangem Ngassa
Department of Chemistry, Grand Valley State University, 1 Campus Drive, Allendale, MI 49401, USA
https://orcid.org/0000-0001-8246-3639

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.


icon graph This Abstract was viewed 1789 times | icon graph Article PDF downloaded 758 times icon graph Article CIF FILE downloaded 0 times icon graph Article CIF FILE downloaded 0 times icon graph Article CIF FILE downloaded 0 times icon graph Article CIF FILE downloaded 0 times icon graph Article CIF FILE downloaded 0 times icon graph Article CIF FILE downloaded 0 times icon graph Article CIF FILE downloaded 0 times

How to Cite
(1)
Stenfors, B. A.; Ngassa, F. N. The Synthesis and Crystallographic Characterization of 4-Methylbenzenesulfonamide Derivatives. Eur. J. Chem. 2021, 12, 109-116.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Gelmo, P. J. Prakt. Chem. 1908, 77, 369-382.
https://doi.org/10.1002/prac.19080770129

[2]. Domagk, G. Dtsch. Med. Wochenschr. 1935, 61, 250-253.
https://doi.org/10.1055/s-0028-1129486

[3]. Whitby, L. H. Lancet 1938, 231, 1210-1212.
https://doi.org/10.1016/S0140-6736(00)89787-1

[4]. Evans, G. M.; Gaisford, W. Lancet 1938, 232, 14-19.
https://doi.org/10.1016/S0140-6736(00)87996-9

[5]. Apaydın, S.; Török, M. Bioorg. Med. Chem. Lett. 2019, 29, 2042-2050.
https://doi.org/10.1016/j.bmcl.2019.06.041

[6]. Gul, H. I.; Yamali, C.; Sakagami, H.; Angeli, A.; Leitans, J.; Kazaks, A.; Tars, K.; Ozgun, D. O.; Supuran, C. T. Bioorg. Chem. 2018, 77, 411-419.
https://doi.org/10.1016/j.bioorg.2018.01.021

[7]. Scozzafava, A.; Owa, T.; Mastrolorenzo, A.; Supuran, C. Curr. Med. Chem. 2003, 10, 925-953.
https://doi.org/10.2174/0929867033457647

[8]. Vedovato, V.; Talbot, E. P. A.; Willis, M. C. Org. Lett. 2018, 20, 5493-5496.
https://doi.org/10.1021/acs.orglett.8b02445

[9]. Zhao, Y.; Shadrick, W. R.; Wallace, M. J.; Wu, Y.; Griffith, E. C.; Qi, J.; Yun, M.-K.; White, S. W.; Lee, R. E. Bioorg. Med. Chem. Lett. 2016, 26, 3950-3954.
https://doi.org/10.1016/j.bmcl.2016.07.006

[10]. De Luca, L.; Giacomelli, G. J. Org. Chem. 2008, 73, 3967-3969.
https://doi.org/10.1021/jo800424g

[11]. Mukherjee, P.; Woroch, C. P.; Cleary, L.; Rusznak, M.; Franzese, R. W.; Reese, M. R.; Tucker, J. W.; Humphrey, J. M.; Etuk, S. M.; Kwan, S. C.; am Ende, C. W.; Ball, N. D. Org. Lett. 2018, 20, 3943-3947.
https://doi.org/10.1021/acs.orglett.8b01520

[12]. Patel, Z. S.; Stevens, A. C.; Bookout, E. C.; Staples, R. J.; Biros, S. M.; Ngassa, F. N. Acta Crystallogr. E Crystallogr. Commun. 2018, 74, 1126-1129.
https://doi.org/10.1107/S2056989018010290

[13]. Senger, S.; Chan, C.; Convery, M. A.; Hubbard, J. A.; Shah, G. P.; Watson, N. S.; Young, R. J. Bioorg. Med. Chem. Lett. 2007, 17, 2931-2934.
https://doi.org/10.1016/j.bmcl.2007.02.034

[14]. Schwertz, G.; Frei, M. S.; Witschel, M. C.; Rottmann, M.; Leartsakulpanich, U.; Chitnumsub, P.; Jaruwat, A.; Ittarat, W.; Schäfer, A.; Aponte, R. A.; Trapp, N.; Mark, K.; Chaiyen, P.; Diederich, F. Chemistry 2017, 23, 14345-14357.
https://doi.org/10.1002/chem.201703244

[15]. Willcott, M. R. MestRe Nova MestRe Nova. Mestrelab Research S.L. Feliciano Barrera 9B, Bajo, 15706 Santiago de Compostela, Spain. http://www.mestrelab.com. J. Am. Chem. Soc. 2009, 131, 13180-13180.
https://doi.org/10.1021/ja906709t

[16]. APEX2, Bruker AXS Inc. Madison, Wisconsin, USA, 2013.

[17]. SAINT, Bruker AXS Inc. Madison, Wisconsin, USA, 2013.

[18]. Sheldrick, G. M. Acta Crystallogr. C Struct. Chem. 2015, 71, 3-8.
https://doi.org/10.1107/S2053229614024218

[19]. Sheldrick, G. M. Acta Crystallogr. A 2008, 64, 112-122.
https://doi.org/10.1107/S0108767307043930

[20]. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339-341.
https://doi.org/10.1107/S0021889808042726

[21]. Bourhis, L. J.; Dolomanov, O. V.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. Acta Crystallogr. A Found. Adv. 2015, 71, 59-75.
https://doi.org/10.1107/S2053273314022207

[22]. Macrae, C. F.; Sovago, I.; Cottrell, S. J.; Galek, P. T. A.; McCabe, P.; Pidcock, E.; Platings, M.; Shields, G. P.; Stevens, J. S.; Towler, M.; Wood, P. A. J. Appl. Crystallogr. 2020, 53, 226-235.
https://doi.org/10.1107/S1600576719014092

[23]. Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P. A. J. Appl. Crystallogr. 2008, 41, 466-470.
https://doi.org/10.1107/S0021889807067908

[24]. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. J. Appl. Crystallogr. 2006, 39, 453-457.
https://doi.org/10.1107/S002188980600731X

[25]. Bruno, I. J.; Cole, J. C.; Edgington, P. R.; Kessler, M.; Macrae, C. F.; McCabe, P.; Pearson, J.; Taylor, R. Acta Crystallogr. B 2002, 58, 389-397.
https://doi.org/10.1107/S0108768102003324

[26]. Taylor, R.; Macrae, C. F. Acta Crystallogr. B 2001, 57, 815-827.
https://doi.org/10.1107/S010876810101360X

[27]. Krause, L.; Herbst-Irmer, R.; Sheldrick, G. M.; Stalke, D. J. Appl. Crystallogr. 2015, 48, 3-10.
https://doi.org/10.1107/S1600576714022985

[28]. Stenfors, B. A.; Staples, R. J.; Biros, S. M.; Ngassa, F. N. Chemistry 2020, 2, 591-599.
https://doi.org/10.3390/chemistry2020036

[29]. Stenfors, B. A.; Staples, R. J.; Biros, S. M.; Ngassa, F. N. Acta Crystallogr. E Crystallogr. Commun. 2020, 76, 452-455.
https://doi.org/10.1107/S205698902000208X

[30]. Stenfors, B. A.; Staples, R. J.; Biros, S. M.; Ngassa, F. N. Acta Crystallogr. E Crystallogr. Commun. 2020, 76, 235-238.
https://doi.org/10.1107/S2056989020000535

[31]. Stenfors, B. A.; Collins, R. C.; Duran, J. R. J.; Staples, R. J.; Biros, S. M.; Ngassa, F. N. Acta Crystallogr. E Crystallogr. Commun. 2020, 76, 1070-1074.
https://doi.org/10.1107/S2056989020007756

[32]. Yang, L.; Powell, D. R.; Houser, R. P. Dalton Trans. 2007, 955-964.
https://doi.org/10.1039/B617136B

[33]. Gowda, B. T.; Foro, S.; Nirmala, P. G.; Terao, H.; Fuess, H. Acta Crystallogr. Sect. E Struct. Rep. Online 2009, 65, o1219.
https://doi.org/10.1107/S1600536809016377

[34]. Modarresi-Alam, A. R.; Amirazizi, H. A.; Bagheri, H.; Bijanzadeh, H.-R.; Kleinpeter, E. J. Org. Chem. 2009, 74, 4740-4746.
https://doi.org/10.1021/jo900454a

Supporting Agencies

National Science Foundation (Grant No. MRI CHE-1725699), Grand Valley State University Chemistry Department’s Weldon Fund.
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2025 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).