Acetanilide → Diphenylamine

HRID 378208Notes

Reaction equation

HRID 378208 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=O)[CH3:2].C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.C1(C)C=CC=CC=1>[C:1]1([NH:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:7]=[CH:6][CH:5]=[CH:10][CH:2]=1

Participants

5

Reactant 2

HCID 904AcetanilideHCID 11430Potassium Carbonate

Product 1

HCID 11487Diphenylamine

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 1140TolueneSolvent

Procedure

The acetanilide II (13.5 g), the particular aromatic bromide III (25 g), potassium carbonate (13.2 g) and copper iodide (1.9 g) were heated (190° C.) and stirred overnight. After cooling to room temperature toluene was added and the precipitate filtered. The solution was concentrated and the excess of bromide removed by distillation under reduced pressure. The residue was dissolved in ethanol (200 ml), potassium hydroxide (10.3 g) was added and the mixture refluxed overnight. Ethanol was evaporated, the residue dissolved in dichloromethane, and washed with brine. The organic layer was dried over MgSO4 and concentrated to obtain the crude diphenyl amine.

Workup

  1. additionwas added
  2. filtrationthe precipitate filtered
  3. concentrationThe solution was concentrated
  4. customthe excess of bromide removed by distillation under reduced pressure
  5. dissolutionThe residue was dissolved in ethanol (200 ml)
  6. additionpotassium hydroxide (10.3 g) was added
  7. temperaturethe mixture refluxed overnight
  8. customEthanol was evaporated
  9. dissolutionthe residue dissolved in dichloromethane
  10. washwashed with brine
  11. dry with materialThe organic layer was dried over MgSO4
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-94c4ed156f4f495a98c5f4a12618e93c
Source dataset
uspto-grants-2000_02
Patent number
US06030803

Reaction notes

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