Acetic Acid → HCID 13763168, compound

Participants

Reaction Steps

A solution of 2-[(4-methoxyphenyl)methylene]-3-oxobutanoic acid, methyl ester (1.17 g., 5 mmole) in dimethylformamide (5 ml.) is treated with 2-aminothiophenol (695 mg., 5 mmole) and the resulting yellow solution is allowed to stir at room temperature for one hour. It is then treated with acetic acid (0.3 ml., about 5 mmoles) and the reaction is allowed to warm up to 65°. Stirring is continued at this temperature for 24 hours. After cooling to room temperature, the reaction is diluted with ether and washed with water (5×20 ml.), sodium bicarbonate, and brine, and is then dried over anhydrous magnesium sulfate. Evaporation provides a yellow foam which is dissolved in isopropyl ether and allowed to sit under refrigeration for several days. A light yellow crystalline product forms (410 mg.). Recrystallization from isopropyl ether gives an analytically pure sample of 2,5-dihydro-2-(4-methoxyphenyl)-4-methyl-1,5-benzothiazepine-3-carboxylic acid, methyl ester; m.p. 107°-109.5°. TLC (silica gel; ethyl acetate:hexane, 50:50) Rf =0.50.

Provenance & Evidence