[C:1]([CH2:3][N:4]1C(=O)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[S:5]1(=[O:7])=[O:6])#[N:2].[CH3:16][O-:17].[Na+].Cl.[CH3:20][OH:21]>>[C:16]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[S:5]([NH:4][CH2:3][C:1]#[N:2])(=[O:7])=[O:6])([O:21][CH3:20])=[O:17]To a suspension of N-cyanomethylsaccharin (276 g) in methanol (1000 ml) was added dropwise 28% sodium methoxide (145 ml) over 30 minutes at 5°-10° C. After stirring at 5°-10° C. for 1 hour, 6N HCl (ca. 230 ml) was added dropwise maintaining the temperature at 10°-15° C. The resulting crystals were collected by filtration, washed with water and dried in vacuo at 50° C. for 16 hours to give o-carbomethoxy-N-cyanomethylbenzenesulfonamide, 264 g (78.7%).
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