Dimethylformamide → HCID 19921046, compound

HRID 1647826Notes

Reaction equation

HRID 1647826 reaction equation
N1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]C1=O.[H-].[Na+].[N:13]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[N:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].[CH3:35][N:36]([CH3:39])[CH:37]=[O:38]>>[CH2:28]([O:27][C:25]([N:13]([C:4]1([CH3:3])[C:9]2[C:35](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:36]([C:39]2[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=2)[C:37]1=[O:38])[NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[O:26])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 755571,2-Bis(phenylmethyl) 1,2-diazenedicarboxylateHCID 321710Oxindole

Product 1

HCID 19921046HCID 19921046, compound

Conditions

Temperature
5 °C

Procedure

After 8.5 g (0.00385 mole) of the indolinone derivative obtained in the above Reference example 18 were dissolved in 60 ml of dimethylformamide and 1.92 g (0.00502 mole) of sodium hydride (a 62.7% mineral oil dispersion) were added to the solution under argon atmosphere under ice cooling, the mixture was stirred at 5° C. for 20 minutes. Next, to the mixture was added 13.6 g of dibenzyl azodicarboxylate, and the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was poured into aqueous ammonia-ice, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then with a saline solution, and dried over anhydrous sodium sulfate. Ethyl acetate was removed under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:ethyl acetate:hexane (1:3 to 1:1 v/v)) to obtain 20.4 g of the title compound as a colorless caramel-like product. MS (DI, m/z): 239 (M+)

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. customAfter completion of the reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialwith a saline solution, and dried over anhydrous sodium sulfate
  6. customEthyl acetate was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent:ethyl acetate:hexane (1:3 to 1:1 v/v))

Sources & evidence

ORD record
ord-0ab13d7973194f32a7bfe4b41bd76771
Source dataset
uspto-grants-1995_07
Patent number
US05434148

Reaction notes

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