Chloromethyl phenyl sulphide → 1,1-Dioxo-2-propan-2-yl-1,2-benzothiazol-3-one

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C([C:4]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:5]=1[C:6](=[O:15])[NH:7][S:8]2(=[O:10])=[O:9])(C)C.ClCS[C:19]1[CH:24]=CC=C[CH:20]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH:19]([N:7]1[C:6](=[O:15])[C:5]2[C:11](=[CH:12][CH:13]=[CH:14][CH:4]=2)[S:8]1(=[O:9])=[O:10])([CH3:24])[CH3:20]

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실험 절차

A mixture of 4-isopropylsaccharin (37.9 g), phenyl chloromethyl sulfide (33.3 g), tetrabutylammonium bromide (5.4 g) and toluene (200 mL) was heated under reflux for 24 hours, then stripped of volatiles. Column chromatography of the residue on silica gel (485 g) and elution first with hexane, then hexane-dichloromethane (1:1), then dichloromethane gave in the hexane-dichloromethane eluate 2-phenylthiomethyl-4,-isopropylsaccharin as a pale yellow oil (53.5 g, 92% yield).