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

doi:10.5155/EURJCHEM.11.3.245-249.2017

Paper

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

Published Sep 30, 2020 · Brock A. Stenfors, F. Ngassa

European Journal of Chemistry

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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.

Study Snapshot

A one-pot synthesis of substituted N-benzyl-4-methylbenzenesulfonamides from 4-methylbenzenesulfonyl chloride has been developed, leading to the crystal structure of N-allyl-N-benzyl-4-methylbenzenesulfon

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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

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Citations

Sulfonamides and sulfonate esters: Synthetic routes, proposed mechanisms, and crystallographic characterizations

This review explores synthetic routes, mechanisms, and crystallographic characterizations of sulfonamides and sulfonate esters, enhancing our understanding of their structural nuances and guiding informed design strategies in synthetic and medicinal chemistry.