Sodium Carbonate → 4-Methyltriphenylamine

HRID 1419671Notes

Reaction equation

HRID 1419671 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-].[Na+].[Na+]>[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 10340Sodium CarbonateHCID 11487DiphenylamineHCID 122074-Iodotoluene

Product 1

HCID 112999284-MethyltriphenylamineYield 81.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

To 30 ml of o-dichlorobenzene, 4.5 g (27 mmol) of diphenylamine, 11.0 g (51 mmol) of p-iodotoluene, 5.5 g (40 mmol) of anhydrous sodium carbonate and 1.1 g of copper powder were added. The mixture was heated and refluxed with stirring for 7 hours. After the reaction was completed, the reaction solution was filtered. The filtrate was successively washed with an aqueous 35% sodium thiosulfate solution and saturated brine. The organic layer was dried with anhydrous sodium sulfate, and thereafter the solvent was removed. The resulting crude reaction product was recrystallized from ethanol to obtain 4-methyltriphenylamine in an amount of 5.7 g (yield: 81.4%).

Workup

  1. temperatureThe mixture was heated
  2. temperaturerefluxed
  3. filtrationthe reaction solution was filtered
  4. washThe filtrate was successively washed with an aqueous 35% sodium thiosulfate solution and saturated brine
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. customthe solvent was removed
  7. customThe resulting crude reaction product
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-d3ea1dbbc35f4f42bf781833df6dc820
Source dataset
uspto-grants-1999_03
Patent number
US05888690

Reaction notes

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