Benzyl Bromide → HCID 22012989, compound

HRID 1533707Notes

Reaction equation

HRID 1533707 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:28])([O:6][C:7]([CH2:9][C:10]1([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]1=[O:19])=[O:8])[CH3:5].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C)C=O>[CH2:29]([N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH2:9][C:7]([O:6][C:4]([CH3:28])([CH3:3])[CH3:5])=[O:8])([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:11]1=[O:19])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 22013049HCID 22013049, compound

Product 1

HCID 22012989HCID 22012989, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.05 g of sodium hydride (60%) in 5 ml of N,N-dimethylformamide was added dropwise a solution of 0.36 g of 3,3-bis((1,1-dimethylethoxy)carbonylmethyl)indolin-2-one in 5 ml of N,N-dimethylformamide at 0° C. in a nitrogen stream. After stirring the mixture at that temperature for 30 minutes, 0.12 ml of benzyl bromide was added thereto. The whole mixture was stirred for 1 hour and then concentrated. Chloroform was added to the concentrate, and the mixture was washed with an aqueous solution of sodium chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain 1-benzyl-3,3-bis((1,1-dimethylethoxy)carbonylmethyl)indolin-2-one.

Workup

  1. stirringThe whole mixture was stirred for 1 hour
  2. concentrationconcentrated
  3. additionChloroform was added to the concentrate
  4. washthe mixture was washed with an aqueous solution of sodium chloride
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-70d9fed7e50244bba92e5613eabe637d
Source dataset
uspto-grants-2001_03
Patent number
US06207836B1

Reaction notes

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