European Journal of Chemistry 2020, 11(3), 245-249 | doi: https://doi.org/10.5155/eurjchem.11.3.245-249.2017 | Get rights and content






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


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: 05 Aug 2020 | Revised: 21 Aug 2020 | Accepted: 22 Aug 2020 | Published: 30 Sep 2020 | Issue Date: September 2020

Abstract


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.


Keywords


Sulfa drug; Benzylation; Amino acids; Sulfonamide; Environmentally benign; Nucleophilic substitution

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DOI: 10.5155/eurjchem.11.3.245-249.2017

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Funding information


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

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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. 2020, 11(3), 245-249. doi:10.5155/eurjchem.11.3.245-249.2017
Stenfors, B.; Ngassa, F. Synthesis and crystallographic characterization of N-allyl-N-benzyl-4-methylbenzenesulfonamide. Eur. J. Chem. 2020, 11(3), 245-249. doi:10.5155/eurjchem.11.3.245-249.2017
Stenfors, B., & Ngassa, F. (2020). Synthesis and crystallographic characterization of N-allyl-N-benzyl-4-methylbenzenesulfonamide. European Journal of Chemistry, 11(3), 245-249. doi:10.5155/eurjchem.11.3.245-249.2017
Stenfors, Brock, & Felix Nyuangem Ngassa. "Synthesis and crystallographic characterization of N-allyl-N-benzyl-4-methylbenzenesulfonamide." European Journal of Chemistry [Online], 11.3 (2020): 245-249. Web. 3 Dec. 2020
Stenfors, Brock, AND Ngassa, Felix. "Synthesis and crystallographic characterization of N-allyl-N-benzyl-4-methylbenzenesulfonamide" European Journal of Chemistry [Online], Volume 11 Number 3 (30 September 2020)

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DOI Link: https://doi.org/10.5155/eurjchem.11.3.245-249.2017

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