2-(N-allylsulfamoyl)-N-propylbenzamide

Abstract

In this work, a new compound, 2-(N-allylsulfamoyl)-N-propylbenzamide, has been synthesized via a tandem one-pot reaction under sonication. The rotational orientations of the allylsulfamoyl and the amide groups in the title molecule, C13H18N2O3S, are partly determined by an intramolecular N—H···O hydrogen bond. In the crystal, a layer structure is generated by N—H···O and C—H···O hydrogen bonds plus C—H···π (ring) interactions. A Hirshfeld surface analysis indicates that the most important contributions to crystal packing are from H···H (59.2%), H···O/O···H (23.5%), and H···C/C···H (14.6%) interactions. The optimized structure calculated using density functional theory at the B3LYP/6–311 G (d,p) level is compared with the experimentally determined structure in the solid state. The calculated highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy gap is 5.3828 eV.

(3-(4-Chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl Benzenesulfonate

“…Inspired by our previous works [26,27], the one-pot synthesis of our product (5) started with the sulfonylation of equimolar equivalents of allylic alcohol (1) and benzene sulfonyl chloride (2) in water with NaOH as a base at 25 • C under sonication to produce the corresponding dipolarophile (3) in situ. Subsequently, in the second step, the alkene sulfonate (3) reacted with p-chlorobenzaldoxime (4) via 1,3-dipolar cycloaddition using NaCl as a precatalyst generated from the first step and oxone as a terminal oxidant to successfully generate the expected (3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl benzenesulfonate (5) as white crystals at a 85% yield (Scheme 1).…”