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

HRID 989410Notes

Reaction equation

HRID 989410 reaction equation
[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]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 23665647Potassium tert-butoxide2×HCID 69509829HCID 69509829, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-701d0ed71c6d4a259ed2c6a6036fbc56
Source dataset
uspto-grants-2003_10
Patent number
US06638965B2

Reaction notes

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