Cesium carbonate → 4-Isopropyl-6-hydroxy-2-phenylthiomethylsaccharin

HRID 129043

반응식

HRID 129043 반응식
[OH:1][C:2]1[CH:12]=[C:11]2[C:5]([C:6](=[O:13])[NH:7][S:8]2(=[O:10])=[O:9])=[C:4]([CH:14]([CH3:16])[CH3:15])[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:23]1([S:29][CH2:30]Cl)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO>[CH:14]([C:4]1[CH:3]=[C:2]([OH:1])[CH:12]=[C:11]2[C:5]=1[C:6](=[O:13])[N:7]([CH2:30][S:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[S:8]2(=[O:10])=[O:9])([CH3:16])[CH3:15]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 81623Chloromethyl phenyl sulphideHCID 100373464-Isopropyl-6-hydroxysaccharin

생성물 1

HCID 103166544-Isopropyl-6-hydroxy-2-phenylthiomethylsaccharin수율 69.9%

시약·촉매·용매 1

HCID 887Methanol용매

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.

후처리

  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

출처 및 근거

ORD 기록
ord-477571b6faaf4165a8249dfb292351a1
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466701

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