o-Chlorophenylacetic acid → Acetyl chloride, 2-(2-chlorophenyl)-

関与物質

反応手順

To 2-chlorophenylacetic acid (0.44 g) is added thionyl chloride (15 ml), and the mixture is stirred at room temperature for 2 hours. Thionyl chloride is distilled off, and the resultant is further distilled off by subjecting twice to azeotrophy with toluene. The resulting residue is dissolved in dichloromethane (10 ml). Separately, to a solution of 5-dimethylamino-1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.40 g) in dichloromethane is added triethylamine (0.36 ml) under ice-cooling, and thereto is added dropwise the above obtained 2-(2-chlorophenyl)acetyl chloride solution. After addition, the mixture is stirred at room temperature for one hour, washed twice with water, dried over magnesium sulfate, and concentrated. The resulting residue is purified by silica gel column chromatography (eluent; chloroform:methanol=200:1), and recrystallized from methanol/diethyl ether to give 5-dimethylamino-1-{4-[2-(2-chlorophenyl)acetylamino]benzoyl}-2,3,4,5-tetrahydro-1H-benzazepine (0.29 g) as white powder, mp. 187°-189° C.

情報源と証拠