反应详情

6-hydroxy-4-isopropylsaccharin (30.0 g, 0.12 mol) in methanol was treated with Cs2CO3 (20.28 g, 0.062 mol). The mixture was stirred at ambient temperature for 3-4 hours, the excess methanol was removed under reduced pressure and the residue was dried under high vacuum. The residue was dissolved in DMF and chloromethyl phenyl sulfide (21.72 g, 0.14 mol) was added. The mixture was heated at 70°-80° C. for 24 hours, cooled, treated with ice-water and extracted with ethyl acetate/ether. The organic layer was washed with water, then brine and was dried. The solvent was removed in vacuo and the residue was purified by column chromatography on silica eluting with ethyl acetate/hexane to afford 30.5 g (67%) of 4-isopropyl-6-hydroxy-2-phenylthiomethylsaccharin.

1. customthe excess methanol was removed under reduced pressure
2. customthe residue was dried under high vacuum
3. dissolutionThe residue was dissolved in DMF
4. temperatureThe mixture was heated at 70°-80° C. for 24 hours
5. temperaturecooled
6. extractionextracted with ethyl acetate/ether
7. washThe organic layer was washed with water
8. dry with materialbrine and was dried
9. customThe solvent was removed in vacuo
10. customthe residue was purified by column chromatography on silica eluting with ethyl acetate/hexane