N-(2,5-Dimethylphenyl)acetamide → 4'-(2-Bromoacetyl)-2',5'-dimethylacetanilide

HRID 275995

Reaction equation

HRID 275995 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][CH2:6][C:7](Br)=[O:8].[CH3:10][C:11]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:12]=1[NH:13][C:14](=[O:16])[CH3:15]>C(=S)=S>[Br:5][CH2:6][C:7]([C:19]1[C:18]([CH3:21])=[CH:17][C:12]([NH:13][C:14](=[O:16])[CH3:15])=[C:11]([CH3:10])[CH:20]=1)=[O:8]

Participants

5

Reactant 3

HCID 16304N-(2,5-Dimethylphenyl)acetamideHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 221696594'-(2-Bromoacetyl)-2',5'-dimethylacetanilide

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a stirred suspension of aluminum chloride (13.4 g) in carbon disulfide (68 ml) was added bromoacetyl bromide (8.8 ml) under ice-cooling, and the mixture was stirred for 30 minutes. 2′,5′-Dimethylacetanilide (5.57 g) was added to the stirred mixture, and the mixture was heated under reflux for 12 hours. After cooling, the reaction mixture was poured into ice-water, and the resulting precipitate were collected by filtration and washed with water. The cake was dissolved in ethyl acetate, and the solution was dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was washed with diethyl ether to give 4′-(2-bromo-acetyl)-2′,5′-dimethylacetanilide (5.65 g).

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 12 hours
  4. temperatureAfter cooling
  5. filtrationthe resulting precipitate were collected by filtration
  6. washwashed with water
  7. dissolutionThe cake was dissolved in ethyl acetate
  8. dry with materialthe solution was dried over anhydrous magnesium sulfate
  9. customAfter removal of the solvent
  10. washthe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-dd964d24ca9e407fad200a61a0fba108
Source dataset
uspto-grants-2002_03
Patent number
US06353025B1

Linked notes

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