Methanol → HCID 20228201, compound

Participants

Reaction Steps

6-(2-Carboxyethyl)-10,11-dihydrodibenz-[b,f]thiepin-3-carboxylic acid (328 mg; 1 mmole) was treated with thionyl chloride (6 ml) and after heating the mixture under reflux for 2 hours excess thionyl chloride was removed under vacuum. The residue was dissolved in 1,2-dichloroethane and the solvent was evaporated off to remove the last traces of thionyl chloride. The crude acid chloride dissolved in 1,2-dichloroethane (5 ml) was treated at 0°-5° C. with anhydrous aluminum chloride (100 mg; 0.75 mmole) in 1,2-dichloroethane (2 ml). The mixture was stirred in the ice-bath for 2 hours and then it was treated with methanol (4 ml). The mixture was stirred in the ice-bath for 5 minutes, then at room temperature for 30 minutes and finally at 50° C. for 30 minutes. Ethyl acetate (20 ml) was added and the solution was washed in succession with 2N hydrochloric acid (2×6 ml), water (6 ml), N sodium (2×6 ml) and finally with water (6 ml). Evaporation of the dried (MgSO4) ethyl acetate solution gives 291 mg of crude product which on purification by column chromatography (10 g Merck silica gel eluted with 3% ethyl acetate in methylene chloride) gave 228 mg (70%) of solid m.p. 156°-158° C.

Provenance & Evidence