m-Chloroperbenzoic acid → HCID 10293318, compound

Reaction equation

[F:1][C:2]([F:25])([F:24])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14][C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[CH:8]=1.ClC1C=CC=C(C(OO)=[O:34])C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:25][C:2]([F:24])([F:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14]([C:15]2[NH:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)=[O:34])[CH:8]=1

Participants

Procedure

The thus-obtained 2-[4-(4,4,4-trifluorobutoxy)pyridin-2-yl-methylthio]-1H-benzimidazole (1.27 g) was dissolved in methylene chloride (20 mL). A solution of 80% m-chloroperbenzoic acid (746 mg) in methylene chloride (10 mL) was added dropwise at −30° C., and the mixture was stirred for an hour at the same temperature. A saturated sodium bicarbonate solution (30 mL) was added to the reaction mixture. The temperature of the mixture was returned to room temperature, and the mixture was stirred for 10 minutes, followed by extraction with methylene chloride. The organic layer was washed sequentially with water and brine, and brought to dryness over sodium sulfate anhydrate. The solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography (silica gel: NH-DM1020 (product of Fuji Silicia), chloroform:methanol=10:1), whereby 2-[4-(4,4,4-trifluorobutoxy)pyridin-2-yl-methanesulfinyl]-1H-benzimidazole was obtained (1.2 g).