Hydrochloric Acid → HCID 20033703, compound

Participants

Reaction Conditions

Reaction Steps

Ethanethiol (2.1 ml, 0.028 mol) was added dropwise over a 10 minute period to a stirred suspension of 60% NaH in mineral oil (1.4 g, 0.035 mol) in dimethylformamide (50 ml) at ice bath temperature under a nitrogen atmosphere. After the sodium hydride had reacted, 4-(1-hydroxyethyl-5-(4-methoxyphenylsulfonyl)thiophene-2-sulfonamide (2.64 g, 0.007 mol) was added to the solution and the solution was heated in an oil bath at 80° C. for 31/2 hours. The solution was cooled to ice bath temperature and 3N HCl was added (20 ml). The acidic mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with saturated NaCl, saturated NaHCO3 and again with saturated NaCl, dried, filtered and concentrated in vacuo. The crude amber oil obtained was washed with pet. ether several times to remove mineral oil and was solidified by trituration in nitromethane. A white solid was obtained, 2.2 g. Recrystallization from nitromethane gave material of mp 173°-175° C. Yield 87%. Purity and structure were confirmed by HPLC, C, H, N analyses and NMR.

Provenance & Evidence