2,5-Dimethylaniline → N-(2,5-Dimethylphenyl)acetamide

HRID 275994

Reaction equation

HRID 275994 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH2:4].[C:10](OC(=O)C)(=[O:12])[CH3:11]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH:4][C:10](=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 72592,5-DimethylanilineHCID 7918Acetic Anhydride

Product 1

HCID 16304N-(2,5-Dimethylphenyl)acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,5-dimethylaniline (5.30 g) and 4-dimethylaminopyridine (6.41 g) in dichloromethane (90 ml) was added acetic anhydride (4.13 ml) under ice-cooling, and the mixture was stirred for 4 hours. The reaction mixture was washed with 1N hydrochloric acid and a saturated aqueous sodium bicarbonate solution subsequently, and dried over anhydrous magnesium sulfate. Removal of the solvent in vacuo gave 2′,5′-dimethylacetanilide (6.09 g).

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed with 1N hydrochloric acid
  3. dry with materiala saturated aqueous sodium bicarbonate solution subsequently, and dried over anhydrous magnesium sulfate
  4. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-e1d948e4bff14b87b806b0d181e33941
Source dataset
uspto-grants-2002_03
Patent number
US06353025B1

Linked notes

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