[CH2:1]([O:8][C:9]1[S:13][N:12]=[C:11]([S:14][CH3:15])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:24])C=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[S:13][N:12]=[C:11]([S:14]([CH3:15])=[O:24])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Into 12 ml of chloroform was dissolved 1.39 g of 5-benzyloxy-3-methylthio-1,2,4-thiadiazole, and metachloroperbenzoic acid (>70%) was slowly added to the mixture under ice-cooling. After stirring for 1 hour, the compound of low-polarity from the reaction mixture was detected by thin layer chromatography. The reaction mixture was poured into a saturated sodium sulfite aqueous solution, and separated. The organic layer was washed with sodium hydrogen carbonate aqueous solution, dried over anhydrous sodium sulfate, concentrated to give 1.4 g of 5-benzyloxy-3-methylsulfinyl-1,2,4-thiadiazole.
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