Hydrochloric Acid → HCID 20033717, compound

Participants

Reaction Steps

Ethanethiol (2.1 ml, 0.028 mol) was added dropwise over 10 minutes to a stirred suspension of 60% NaH in mineral oil (1.28 g, 0.032 mol) in DMF (30 ml) at ice bath temperature under nitrogen. After the sodium hydride had reacted, 4-(1-hydroxyethyl)-5-(4-methoxyphenylthio)thiophene-2-sulfonamide (1.0 g, 0.0029 mol) was added and the solution was stirred at steam bath temperature over night. The mixture was cooled in ice and acidified with 3N HCl (20 ml). The mixture was extracted with ethyl acetate and the extract was washed with saturated NaCl, saturated NaHCO3 and again with saturated NaCl. The extract was dried, filtered and concentrated in vacuo. The residual oil was washed with pet ether to remove the mineral oil and was purified by silica gel chromatography using 10% methanol in chloroform. The white solid product was obtained in 61% yield, mp. 133°-137° C. Purity and structure were confirmed by HPLC, C, H, N analysis and NMR.

Provenance & Evidence