Hydrochloric Acid → Thieno[2,3-c]pyridine-2-sulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of potassium ferricyanide (76 g, 0.23 mol) in water (400 ml) was added a solution of potassium hydroxide (68 g, 0.113 mol) in water (150 ml), followed by a suspension of 2-sulfamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (10.8 g, 49.5 mmol) in water (50 ml). This mixture was warmed at 80° C. for 4-6 hours. This solution was acidified with concentrated hydrochloric acid and then made basic with saturated sodium carbonate solution. The product was extracted from this solution with ethyl acetate. The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered through a pad of charcoal and evaporated to give 5.5 g of crude product. This material was chromatographed on silica gel and eluted with ethyl acetate to give 3.7 g (34.9% yield) of pure product; m.p. 191°-193° C.

Provenance & Evidence