Benzenesulfonamide → 2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]-N-(phenylsulphonyl)thiazole-5-carboxamide

Participants

Reaction Steps

1-(3--Dimethylaminopropyl)ethylcarbodiimide hydrochloride (0.85 g) was added to a stirred mixture of 2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]thiazole-5-carboxylic acid (1 g), benzenesulphonamide (0.35 g), 4-dimethylaminopyridine (0.27 g) and triethylamine (0.225 g) in N,N-dimethylformamide (100 mL) and the mixture was stirred at ambient temperature for 16 hours. Water (30 mL) was added to the reaction mixture which was then extracted three times with ethyl acetate (20 mL each time). The combined ethyl acetate extracts were washed consecutively with aqueous 2N HCL (3×10 mL), aqueous saturated NaHCO solution (3×10 mL) and water (10 mL) and dried. The residue obtained on evaporation of the solvent was filtered through silica using ethyl acetate as eluant. The solvent was evaporated and on trituration with diethyl ether the residue gave 2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]-N-(phenylsulphonyl)thiazole-5-carboxamide, yield 0.358 g, mp 140°-145° C.

Provenance & Evidence