Potassium Carbonate → 4-Methyltriphenylamine

HRID 399697Notes

Reaction equation

HRID 399697 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.I[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].ClC1C=CC=CC=1Cl>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([N:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11487DiphenylamineHCID 122074-Iodotoluene

Product 1

HCID 112999284-MethyltriphenylamineYield 81.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

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

Workup

  1. temperatureto heating
  2. temperaturerefluxing for 7 hours under stirring conditions
  3. customUpon completion of the reaction
  4. filtrationthe reaction solution was filtered
  5. washthe filtrate was washed with a 3-5% aqueous solution of sodium thiosulfate
  6. dry with materialAfter drying the organic layer with anhydrous sodium sulfate
  7. customthe solvent was removed
  8. customThe reaction mixture obtained
  9. customwas recrystallized with ethanol

Sources & evidence

ORD record
ord-84734a60c3e347b5b52c35395c312fff
Source dataset
uspto-grants-1998_10
Patent number
US05824443

Reaction notes

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