반응 #216225

반응 방정식

chloromethyl phenyl sulfide

6-hydroxy-4-isopropylsaccharin

Cs2CO3

→

4-isopropyl-6-hydroxy-2-phenylthiomethylsaccharin

수율 69.9%

용매

methanol

반응 조건

후처리

1. 1
   기타the excess methanol was removed under reduced pressure
2. 2
   기타the residue was dried under high vacuum
3. 3
   workup.DISSOLUTIONThe residue was dissolved in DMF
4. 4
   온도The mixture was heated at 70°-80° C. for 24 hours
5. 5
   온도cooled
6. 6
   추출extracted with ethyl acetate/ether
7. 7
   세척The organic layer was washed with water
8. 8
   건조brine and was dried
9. 9
   기타The solvent was removed in vacuo
10. 10
    기타the residue was purified by column chromatography on silica eluting with ethyl acetate/hexane

실험 절차

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.

출처