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

HRID 129043

反応式

HRID 129043 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 103166544-Isopropyl-6-hydroxy-2-phenylthiomethylsaccharin収率 69.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-477571b6faaf4165a8249dfb292351a1
出典データセット
uspto-grants-1995_11
特許番号
US05466701

関連ノート

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