Isatin → 1-Benzylisatin

HRID 618528Notes

Reaction equation

HRID 618528 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[CH2:14]([N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7054IsatinHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 2647341-BenzylisatinYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 44 g of isatin in 200 ml of N,N-dimethylformamide was added dropwise to a suspension of 16.0 g of sodium hydride (60%) in 100 ml of N,N-dimethylformamide at 0° C. in a nitrogen stream. After the mixture was stirred at that temperature for 30 minutes, a solution of 61.5 g of benzyl bromide in 100 ml of N,N-dimethylformamide was added thereto. The whole mixture was stirred for 1 hour and then concentrated. Chloroform was added to the residue, and the mixture was washed with saturated aqueous sodium hydrogencarbonate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting crude product was washed with hexane and recrystallized from ethanol to give 47.3 g (67%) of the title compound as red needles.

Workup

  1. stirringThe whole mixture was stirred for 1 hour
  2. concentrationconcentrated
  3. additionChloroform was added to the residue
  4. washthe mixture was washed with saturated aqueous sodium hydrogencarbonate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. washThe resulting crude product was washed with hexane
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-faafe2d38ebf4c14ba34c3946f5aaac1
Source dataset
uspto-grants-1999_09
Patent number
US05952511

Reaction notes

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