I([O-])(=O)(=O)=[O:2].[Na+].[CH3:7][C:8]1([CH3:27])[NH:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=2)[C:9]1=[O:26]>O.O1CCCC1>[CH3:21][S:20]([C:17]1[CH:18]=[CH:19][C:14]([N:10]2[C:9](=[O:26])[C:8]([CH3:27])([CH3:7])[NH:12][C:11]2=[O:13])=[CH:15][C:16]=1[C:22]([F:25])([F:24])[F:23])=[O:2]470 mg of sodium periodate were dissolved in 5 ml of water and admixed slowly with 640 mg of 114.1, dissolved in 10 ml of tetrahydrofuran, with ice bath cooling. The mixture was stirred at room temperature overnight. Another 210 mg of sodium periodate were added and the mixture was stirred for a further 8 h. Thereafter, the reaction mixture was admixed with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The chromatographic purification (silica gel; 96/4 dichloromethane/methanol) afforded 3-(4-methanesulfinyl-3-trifluoromethylphenyl)-5,5-dimethylimidazolidine-2,4-dione (114.1a). Molecular weight 334.05 (C13H13F3N2O3S); retention time Rt=1.69 min. [B]; MS (ES−): 335.19 (M−H+).
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