Benzenesulfonamide → HCID 19806374, compound

Participants

Reaction Steps

4-[(2-Butyl-1H-benzimidazol-1-yl)methyl]benzoic acid (150 mg) was added to a solution of benzenesulphonamide (79 mg), dimethylaminopyridine (60 mg) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (91 mg) in dry dichloromethane (5 ml). The mixture was stirred overnight and then diluted with dichloromethane (20 ml). The solution was washed successively with 1M hydrochloric acid (20 ml), water (20 ml) and saturated brine (20 ml), and then dried (MgSO4). The solvent was removed by evaporation and the residue triturated with ether to give 4-[(2-butyl-1H-benzimidazol-1-yl)methyl]-N-phenylsulphonylbenzamide as a white solid, m.p. 241°-242° C.; NMR (d6 -DMSO): 0.9(t,3H), 1.35(m,2H), 1.7(m,2H), 2.85(t,2H), 5.6(s,2H), 7.2(m,3H), 7.4(m,1H), 7.6(m,4H). 7.8(d,2H), 8.0(d,2H); mass spectrum (-ve FAB, DMSO/m-nitrobenzyl alcohol): 446(M-H)- ; microanalysis found: C,66.7; H,5.6; N,9.1; C25H25N3O3S requires: C,67.1; H,5.6; N,9.4%.

Provenance & Evidence