European Journal of Chemistry

The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives

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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
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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.


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

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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.
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