3,4-Dimethylaniline → 3',4'-Dimethylacetanilide

HRID 2291105Notes

Reaction equation

HRID 2291105 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH3:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=1[CH3:16])[NH2:12]>C(O)(=O)C>[CH3:16][C:15]1[CH:14]=[CH:13][C:11]([NH:12][C:5]([CH3:6])=[O:7])=[CH:10][C:9]=1[CH3:8]

Participants

4

Reactant 2

HCID 72483,4-DimethylanilineHCID 7918Acetic Anhydride

Product 1

HCID 751443',4'-Dimethylacetanilide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

95 ml of acetic anhydride was added to a stirred solution of 3,4-dimethylaniline in 300 ml of glacial acetic acid at such a rate the temperature of the mixture slowly rose to 60° C. The resulting mixture was stirred while the temperature dropped to room temperature, then evaporated to dryness. A mixture of water and ice was added to the residue, followed by methylene chloride. The resulting mixture was stirred and treated with solid sodium bicarbonate until neutral. The organic phase was separated, and dried (MgSO4), and the solvent was evaporated to give 3,4-dimethylacetanilide (4A).

Workup

  1. customslowly rose to 60° C
  2. additiondropped to room temperature
  3. customevaporated to dryness
  4. additionA mixture of water and ice
  5. additionwas added to the residue
  6. stirringThe resulting mixture was stirred
  7. additiontreated with solid sodium bicarbonate until neutral
  8. customThe organic phase was separated
  9. dry with materialdried (MgSO4)
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a0ffb6e6f85146168e7a5c458dca12dd
Source dataset
uspto-grants-1986_10
Patent number
US04620000

Reaction notes

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