Sodium hydride → HCID 22711892, compound

HRID 352367Notes

Reaction equation

HRID 352367 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[C:6]([Br:14])[CH:5]=1)(=[O:3])[CH3:2].[H-].[Na+].Br[CH2:18][C:19]([CH3:21])=[CH2:20]>CN(C=O)C>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:20][C:19]([CH3:21])=[CH2:18])[C:11](=[O:13])[CH3:12])=[C:6]([Br:14])[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3577853-Bromo-2-methyl-1-propeneHCID 36824744-Acetamido-3-bromoacetophenone

Product 1

HCID 22711892HCID 22711892, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(4-Acetyl-2-bromophenyl)acetamide (25 g, 0.1 mole) in dry DMF (250 ml) was treated with sodium hydride (60%, 4.5 g, 0.11 mole) at 25° C. under argon with stirring for 1 h. 3-Bromo-2-methylpropene (1.1 ml, 0.11 mole) was added and the mixture stirred for a further 16 h. The mixture was concentrated in vacuo and partitioned between water and Et2O. The organic phase was dried and concentrated in vacuo to give the title compound (32.8 g, 100%).

Workup

  1. stirringthe mixture stirred for a further 16 h
  2. concentrationThe mixture was concentrated in vacuo
  3. custompartitioned between water and Et2O
  4. customThe organic phase was dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aaf3b0ffe06442118a5675e293067f49
Source dataset
uspto-grants-2004_06
Patent number
US06747030B1

Reaction notes

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