4,4'-Dimethoxybenzophenone → TAS-301

HRID 1600876Notes

Reaction equation

HRID 1600876 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH3:11][O:12][C:13]1[CH:28]=[CH:27][C:16]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=O)=[CH:15][CH:14]=1.[H-].[Na+].[H][H].[Cl-].[NH4+]>O1CCCC1>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:17]([C:16]2[CH:27]=[CH:28][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])=[CH:24][CH:23]=1

Participants

7

Reactant 5

HCID 70324,4'-DimethoxybenzophenoneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 321710OxindoleHCID 178418361HCID 178418361, compound

Product 1

HCID 9885087TAS-301Yield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.0 g of oxindole was dissolved in 100 ml tetrahydrofuran, and 21.8 g of 4,4'-dimethoxybenzophenone was added thereto at room temperature. Subsequently, the temperature of the reaction was brought to 0° C. 9.0 g of 60% sodium hydride was added, and when generation of hydrogen ceased, the reaction mixture was refluxed with heat for 12 hours. After completion of reaction, the reaction mixture was cooled. Saturated aqueous ammonium chloride solution was added, followed by extraction with ethyl acetate. The extract was washed with water and saturated brine, dried over sodium sulfate, and then evaporated. The resultant crude product was recrystallized from methanol, to thereby obtain 22.8 g (yield 85%) of the title compound in yellow crystals (Crystal 1). The melting point and elementary analysis data are shown in Table 1, and NMR and MS spectrum data are shown in Table 2. Also, the IR spectrum chart of the compound is shown in FIG. 1.

Workup

  1. customat room temperature
  2. customwas brought to 0° C
  3. temperaturethe reaction mixture was refluxed
  4. temperaturewith heat for 12 hours
  5. customAfter completion of reaction
  6. temperaturethe reaction mixture was cooled
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe extract was washed with water and saturated brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated
  11. customThe resultant crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-d8c84c9e640645258b72d54d9a6c6ad1
Source dataset
uspto-grants-1999_11
Patent number
US05977130

Reaction notes

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