Water → (Z)-1-acetyl-3-(1-ethoxy-1-phenyl-methylidene)-5-(N-methyl-N-phenylsulphonyl-amino)-2-indolinone

HRID 989410ノート

反応式

HRID 989410 の反応式
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N:13]([C:23](=O)C)[S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[CH:10][CH:11]=2)[C:6](=[C:26]([O:33][CH2:34][CH3:35])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:5]1=[O:36])(=[O:3])[CH3:2].CC(C)([O-])C.[K+].IC.O>CS(C)=O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N:13]([CH3:23])[S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[CH:10][CH:11]=2)/[C:6](=[C:26](/[O:33][CH2:34][CH3:35])\[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)/[C:5]1=[O:36])(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodide2 回HCID 23665647Potassium tert-butoxide2 回HCID 695098291-acetyl-3-(1-ethoxy-1-phenyl-methylidene)-5-(N-acetyl-N-phenylsulphonyl-amino)-2-indolinone

生成物 1

HCID 18005732(Z)-1-acetyl-3-(1-ethoxy-1-phenyl-methylidene)-5-(N-methyl-N-phenylsulphonyl-amino)-2-indolinone

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

10 g (20 mmol) of 1-acetyl-3-(1-ethoxy-1-phenyl-methylidene)-5-(N-acetyl-N-phenylsulphonyl-amino)-2-indolinone (Example 1e) are dissolved in 150 ml of DMSO and combined with 2.2 g (20 mmol) of potassium tert. butoxide with stirring. After 15 minutes' stirring 1.9 ml (31 mmol) of iodomethane are added. The mixture is stirred for 3 hours at ambient temperature. Then another 2.2 g (20 mmol) of potassium tert. butoxide and 1 ml (16 mmol) of iodomethane are added. The mixture is stirred for 18 hours at ambient temperature. Then water is added. The reaction mixture is extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulphate and evaporated to dryness. The residue is chromatographed on silica gel (petroleum ether/dichloromethane, 7:3).

後処理

  1. additionare added
  2. stirringThe mixture is stirred for 3 hours at ambient temperature
  3. stirringThe mixture is stirred for 18 hours at ambient temperature
  4. extractionThe reaction mixture is extracted with ethyl acetate
  5. washThe organic phase is washed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated to dryness
  8. customThe residue is chromatographed on silica gel (petroleum ether/dichloromethane, 7:3)

出典と根拠

ORDレコード
ord-701d0ed71c6d4a259ed2c6a6036fbc56
出典データセット
uspto-grants-2003_10
特許番号
US06638965B2

反応ノート

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