[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(N([CH2:11][CH3:12])CC)C.S(Cl)([Cl:15])=O.[ClH:17].C(N([CH2:23][CH3:24])CC)C.[O:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[Cl:17][C:24]1[CH:23]=[CH:29][C:28]([Cl:15])=[C:27]([C:11]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH2:12])[C:26]=1[OH:25]To a solution of 99.6 mg (1.4625 mol, 1.5 mol equivalent) of 1H-imidazole and 0.204 ml (1.5 mol equivalent) of triethylamine in 1.5 ml of tetrahydrofuran (hereinafter referred to as "THF") was dropwise added 0.106 ml (1.5 mol equivalent) of thionyl chloride at 13°-17° C. The mixture was stirred at the same temperature for 30 minutes, and after the termination of the reaction the precipitating triethylamine hydrochloride was removed by filtration. The filtrate was dropwise added to a solution of 0.2 g (0.975 mmol) of 3,6-dichloro-2-hydroxy acetophenone 6, 0.163 ml (1.2 mol equivalent) of triethylamine and 0.5 ml of THF at 28°-32° C. The mixture was stirred at the same temperature for 1 hour and evaporated under reduced pressure. The residue was extracted with dichloromethane, and the extract was washed with water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The resulting residue is purified by silica-gel chromatography to give 152 mg (yield: 61.0%) of the titled compound 7.
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