European Journal of Chemistry

Synthesis and crystallographic characterization of N-allyl-N-benzyl-4-methylbenzenesulfonamide


Main Article Content

Brock Anton Stenfors
Felix Nyuangem Ngassa


N-Benzyl-4-methylbenzenesulfonamides were prepared via a two-step synthetic process involving the treatment of 4-methylbenzenesulfonyl chloride with a primary amine to give the corresponding 4-methylbenzenesulfonamide. Benzylation of the sulfonamide affords the substituted N-benzyl-4-methylbenzenesulfonamides. The similarities between the two steps of synthesis lend credence to the development of a one-pot synthesis of substituted N-benzyl-4-methylbenzenesulfonamides from 4-methylbenzenesulfonyl chloride. This method was applied to the synthesis of N-allyl-N-benzyl-4-methylbenzenesulfonamide and characterized through spectroscopic and crystallographic means. The crystal structure of N-allyl-N-benzyl-4-methylbenzenesulfonamide was obtained by single-crystal X-ray diffraction. The crystal structure reveals an orthorhombic Pna21 space group with cell parameters a = 18.6919 (18) Å, b = 10.5612 (10) Å, c = 8.1065 (8) Å, V = 1600.3 (3) Å3 and Z = 4, T = 173.15 K, μ(MoKα) = 0.206 mm-1, Dcalc = 1.251 g/cm3, 14455 reflections measured (4.36° ≤ 2Θ ≤ 54.96°), 3619 unique (Rint = 0.0439, Rsigma = 0.0429) which were used in all calculations. The final R1 was 0.0428 (I > 2σ(I)) and wR2 was 0.1079 (all data). Molecules are linked through C-H···N hydrogen bonds and C-H···π interactions.

icon graph This Abstract was viewed 1015 times | icon graph Article PDF downloaded 582 times icon graph Article CIF FILE downloaded 0 times

How to Cite
Stenfors, B. A.; Ngassa, F. N. Synthesis and Crystallographic Characterization of N-Allyl-N-Benzyl-4-Methylbenzenesulfonamide. Eur. J. Chem. 2020, 11, 245-249.

Article Details

Crossref - Scopus - Google - European PMC

[1]. Parker, M. F.; Barten, D. M.; Bergstrom, C. P.; Bronson, J. J.; Corsa, J. A.; Dee, M. F.; Gai, Y.; Guss, V. L.; Higgins, M. A.; Keavy, D. J.; Loo, A.; Mate, R. A.; Marcin, L. R.; McElhone, K. E.; Polson, C. T.; Roberts, S. B.; Macor, J. E. Bioorg. Med. Chem. Lett. 2012, 22, 6828-6831.

[2]. Hebert, S. S.; Serneels, L.; Dejaegere, T.; Horre, K; Dabrowski, M.; Baert, V.; Annaert, W.; Hartmann, D.; Strooper, B. D. Neurobiol. Dis. 2004, 17, 260-272.

[3]. O'Brien, R. J.; Wong, P. C. Annu. Rev. Neurosci. 2011, 34, 185-204.

[4]. Herrup, K. J. Neurosci. 2010, 30, 16755-16762.

[5]. Yoshioka, H.; Yamada, A.; Nishiyama, Y.; Kagechika, H.; Hashimoto, Y.; Fujii, S. Bioorg. Med. Chem. 2017, 25, 3461-3470.

[6]. Patel, G. C.; Liu, Y.; Millar, J. C.; Clark, A. F. Sci. Rep. 2018, 8, 1-13.

[7]. Lesovaya, E.; Yemelyanov, A.; Swart, A. C.; Swart, P.; Haegeman, G.; Budunova, I. Oncotarget. 2015, 6, 30730-30744.

[8]. Fini, M. E.; Schwartz, S. G.; Gao, X.; Jeong, S.; Patel, N.; Itakura, T.; Price, M. O.; Price Jr., F. W.; Varma, R.; Stamer, W. D. Prog. Ret. Eye Res. 2017, 56, 58-83.

[9]. Willcott, M. R. J. Am. Chem. Soc. 2009, 131, 13180-13180.

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

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

[12]. Sheldrick, G. M. Acta Cryst. A 2015, 71, 3-8.

[13]. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J; Howard, J. A. K.; Puschmann, H. J. Appl. Cryst. 2009, 42, 339-341.

[14]. Bourhis, L. J.; Dolomanov, O. V.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. Acta Cryst. A 2015, 71, 59-75.

[15]. 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. Cryst. 2020, 53, 226-235.

[16]. 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. Cryst. 2008, 41, 466-470.

[17]. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. J. Appl. Cryst. 2006, 39, 453-457.

[18]. Bruno, I. J.; Cole, J. C.; Edgington, P. R.; Kessler, M. K.; Macrae, C. F.; McCabe, P.; Pearson, J.; Taylor, R. Acta Cryst B. 2002, 58, 389-397.

[19]. Taylor, R.; Macrae, C. F. Acta Cryst. B 2001, 57, 815-827.

[20]. Krause, L.; Herbst-Irmer, R.; Sheldrick, G. M.; Stalke, D. J. Appl. Cryst. 2015, 48, 3-10.

[21]. Parsons, S.; Flack, H. D.; Wagner, T. Acta Cryst. B 2013, 69, 249-259.

[22]. Yang, L.; Powell, D. R.; Houser, R. P. Dalton Trans. 2007, 9, 955-956.

Supporting Agencies

Pfizer Inc. and Grand Valley State University, 1 Campus Drive, Allendale, MI 49401, USA.

Dimensions - Altmetric - scite_ - PlumX

Downloads and views


Download data is not yet available.


Metrics Loading ...
License Terms

License Terms


Copyright © 2024 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 and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License ( 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 ( are administered by Atlanta Publishing House LLC (European Journal of Chemistry).