The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives

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.

Light-Driven Reductive Cleavage of Sulfonamides Promoted by Thiourea Organophotosensitizers

“…13 C­{ 1 H} NMR (125 MHz, CDCl 3 ): δ 170.4, 144.9, 136.7, 136.5, 129.8, 128.6, 128.0, 127.8, 49.5, 24.9, 21.6 ppm. Spectroscopic data were consistent with the literature data for this compound …”

“…The crude residue was purified by silica gel column chromatography eluent: EtOAc/Cyclohexane 1:9) to afford compound 4o (124 mg, 0.34 mmol, 60%) as a white solid. 1 49 Compound 4s. According to the representative procedure, starting from p-toluenesulfonamide (1 equiv, 500 mg, 2.92 mmol) and benzoyl chloride (1.1 equiv, 0.37 mL, 3.21 mmol); flash chromatography on silica gel (EtOAc/Cy, 3:7) gave compound 4s (0.75 g, 2.72 mmol, 93%) as a white solid.…”