1,2-Dichlorobenzene → 4-Methyltriphenylamine

HRID 357472Notes

Reaction equation

HRID 357472 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](=O)([O-])[O-].[K+].[K+].Cl[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1Cl>[Cu]>[CH3:14][C:11]1[CH:10]=[CH:9][C:8]([N:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 11430Potassium CarbonateHCID 11487Diphenylamine

Product 1

HCID 112999284-Methyltriphenylamine

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

4.5 g (27 mmol) of diphenylamine, 11.0 g (51 mmol) of piodotoluene, 5.5 g (40 mmol) of anhydrous potassium carbonate, and 1.1 g of copper chips were added to 30 mL of o-dichlorobenzene, and the mixture was refluxed for 7 hours with stirring. Upon completion of the reaction, the solution was filtered, the filtrate was washed with a 3 to 5% aqueous solution of sodium thiosulfate and then with a saturated brine. After drying the organic layer with an anhydrous sodium sulfate, the solvent was removed. The crude product was recrystallized from ethanol, whereby 4-methyltriphenylamine was obtained in an amount of 5.7 g (81.4 %).

Workup

  1. temperaturethe mixture was refluxed for 7 hours
  2. customUpon completion of the reaction
  3. filtrationthe solution was filtered
  4. washthe filtrate was washed with a 3 to 5% aqueous solution of sodium thiosulfate
  5. dry with materialAfter drying the organic layer with an anhydrous sodium sulfate
  6. customthe solvent was removed
  7. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-d2f82166a5264480aaea4ea0441c8fca
Source dataset
uspto-grants-1998_11
Patent number
US05840816

Reaction notes

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