[CH2:1]([N:4]1[C:8]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)=[C:7]([CH:17]([CH3:19])[CH3:18])[N:6]=[C:5]1[CH2:20]OCC1C=CC=CC=1)[CH:2]=[CH2:3].B(Cl)(Cl)[Cl:30].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([N:4]1[C:8]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)=[C:7]([CH:17]([CH3:19])[CH3:18])[N:6]=[C:5]1[CH2:20][Cl:30])[CH:2]=[CH2:3]In 5 ml of methylene chloride was dissolved 470 mg (1.13 mmol) of 1-allyl-2-benzyloxymethyl-5-(3-chlorophenylthio)-4-isopropyl-1H-imidazole (17g), with cooling to -40° C., 0.7 ml (1.36 mmol) of methylene chloride solution of boron trichloride (1.94 molar) was added with stirring, and the mixture was stirred for 30 minutes. To this reaction mixture, a saturated aqueous solution of sodium bicarbonate was added for neutralization, methylene chloride layer was washed with water arid dried over sodium sulfate. The solvent was concentrated under reduced pressure and the residue was fractionated by silica gel chromatography (ethyl acetate: methylene chloride=1:4). From the first fraction, 50 mg (yield 13%) of 1-allyl-2-chloromethyl-5-(3-chlorophenylthio)-4-isopropylimidazole (28a) was obtained as oil, and then, 155 mg (yield 43%) of Compound I-17 was obtained.
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