Sodium hydride → HCID 21481019, compound

HRID 1490339Notes

Reaction equation

HRID 1490339 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[NH:10][C:9](=[O:16])[C:8]2([CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH2:23][CH2:22]1)SC.[CH3:35][O:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=1[O:45][CH3:46])[CH2:40]Cl.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]([CH2:40][C:39]1[CH:42]=[CH:43][C:44]([O:45][CH3:46])=[C:37]([O:36][CH3:35])[CH:38]=1)[C:9](=[O:16])[CH:8]2[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 81740Veratryl chlorideHCID 516892Sodium BicarbonateHCID 21480994HCID 21480994, compound

Product 1

HCID 21481019HCID 21481019, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide was suspended 38 mg of sodium hydride. To the suspension were added 285 mg of 5,6-dimethoxy-3-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-3-methylthio-1,3-dihydro-2(2H)-indolone and 140 mg of 3,4-dimethoxybenzyl chloride. A sodium hydrogencarbonate aqueous solution was added to the reaction mixture, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was dissolved in ethanol. Separately, an acetone solution containing 2.0 g of Raney nickel was refluxed, and the solvent was removed by decantation. To the residue was added the above prepared ethanol solution, followed by refluxing for 15 minutes. A precipitate was removed by filtration, the solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2 to 0:1) to obtain 201 mg of the title compound.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. dissolutionthe residue was dissolved in ethanol
  6. additionSeparately, an acetone solution containing 2.0 g of Raney nickel
  7. temperaturewas refluxed
  8. customthe solvent was removed by decantation
  9. additionTo the residue was added the
  10. customabove prepared ethanol solution
  11. temperatureby refluxing for 15 minutes
  12. customA precipitate was removed by filtration
  13. customthe solvent was evaporated
  14. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2 to 0:1)

Sources & evidence

ORD record
ord-96589fd7ee4046d49a28c2ca0ef65d26
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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