[Br:1][CH2:2][C:3]([NH:5][C:6]1[C:7]([S:15][CH3:16])=[N:8][C:9]([CH3:14])=[CH:10][C:11]=1[S:12][CH3:13])=[O:4].ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)(Cl)Cl.O>[Br:1][CH2:2][C:3]([NH:5][C:6]1[C:7]([S:15]([CH3:16])=[O:25])=[N:8][C:9]([CH3:14])=[CH:10][C:11]=1[S:12][CH3:13])=[O:4]To a solution of 2-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide (100 mg,0.311 mmol) in chloroform (2 ml) was added a solution of m-chloroperbenzoic acid (50 mg, 0.327 mmol) in chloroform (0.5 ml), and stirred at room temperature for 17 hours. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution, water and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:acetone=1:1) to provide 21.4 mg (yield 20%) of 2-bromo-N-[2(methanesulfinyl)-6-methyl-4-(methylthio)-3-pyridyl]acetamide.
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