反応 #5678

反応方程式

2-chlorophenylacetic acid

thionyl chloride

→

2-(2-chlorophenyl)acetyl chloride

反応条件

後処理

1. 1
   workup.DISTILLATIONThionyl chloride is distilled off
2. 2
   workup.DISTILLATIONthe resultant is further distilled off
3. 3
   workup.DISSOLUTIONThe resulting residue is dissolved in dichloromethane (10 ml)
4. 4
   workup.ADDITIONSeparately, 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-
5. 5
   温度cooling
6. 6
   workup.ADDITIONis added dropwise the

実験手順

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.

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