[OH:1]OS([O-])=O.[K+].[CH3:7][S:8][CH2:9][C:10]1[N:11]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[CH:12]=[CH:13][N:14]=1.[OH-:26].[Na+]>CO.O>[CH3:7][S:8]([CH2:9][C:10]1[N:11]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=2)[CH:12]=[CH:13][N:14]=1)(=[O:1])=[O:26]Oxone (Trade mark; potassium peroxymonosulfate: 28.8 g) was added to a suspension of 4-[4-[2-[(methylthio)methyl]-1H-imidazol-1-yl]butyl]phenol (8.64 g) in methanol-water (2:1) (150 ml) at 0° C. and the mixture was stirred at room temperature for 3.5 hr. The reaction mixture was adjusted to pH 6 by addition of 4N aqueous sodium hydroxide solution to precipitate crystals, which were collected by filtration. The crystals were dissolved in ethyl acetate-methanol (1:4), and the insoluble was filtered off. The filtrated was concentrated and recrystallized from ethyl acetate-methanol-hexane to give the titled compound (6.53 g) as colorless needle crystals.
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