OO[S:3]([O-:5])=[O:4].[K+].S([O-])(O[O-])(=O)=O.[K+].[K+].[CH3:15][CH:16]([N:18]1[CH2:23][C:22]2[CH:24]=[C:25](SC)[CH:26]=[CH:27][C:21]=2[NH:20][S:19]1(=[O:31])=[O:30])[CH3:17].[C:32](OCC)(=O)C>O.CC(C)=O.O>[CH3:15][CH:16]([N:18]1[CH2:23][C:22]2[CH:24]=[C:25]([S:3]([CH3:32])(=[O:5])=[O:4])[CH:26]=[CH:27][C:21]=2[NH:20][S:19]1(=[O:31])=[O:30])[CH3:17]A solution of OXONE® (potassium peroxymonosulfate) (5.65 g, 0.0092 mol) in water was added to a solution of 3,4-dihydro-3-(1-methylethyl)-6-(methylthio)-1H-2,1,3-benzothiadiazine-2,2-dioxide (1 g, 0.0037 mol) in acetone/water (25 ml/2.5 ml) stirring at room temperature. After 30 mins, water (25 ml) and ethyl acetate (50 ml) were added to the mixture. The two layers were separated and the organic layer was then dried (MgSO4) and concentrated in vacuo to afford 3,4-dihydro-3-(1-methylethyl)-6-(methylsulfonyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide as a pale yellow solid. δ (1H NMR, CDCl3, 300 MHz, ppm): 1.0 (3H, d), 2.9 (3H, s), 4.1 (1H, m), 4.6 (2H, s), 6.8 (1H, d), 7.6 (2H, m), 9.9 (1H, s).
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