Aniline → Triphenylamine

HRID 270748Notes

Reaction equation

HRID 270748 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[Cu].C1(C)C=CC=CC=1>[C:8]1([N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 10340Sodium CarbonateHCID 11575Iodobenzene

Product 1

HCID 11775TriphenylamineYield 129.3%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1140TolueneSolvent

Procedure

That is, in a two-neck flask of 500 ml in volume, 152.0 g anhydrous sodium carbonate (1.10 mol) and 9.5 g powdery copper (0.15 mol) were added and then heated for 2 hours while stirring to uniform. Subsequently, after cooling to room temperature, the solution was added with 67.6 g of an aniline compound (0.5 mol) represented by the formula (49) described below and 305.9 g of iodobenzene (1.5 mol) and then heated again to 220° C. to allow the reaction for 2.5 hours. After that, the solution was cooled to room temperature and then added with 100 ml toluene, followed by filtration. The resulting residue was dissolved in toluene and dried over activated clay. After that, the residue was dissolved in toluene and then added with methanol to crystallization. Then, the residue was dissolved in toluene again and added with methanol to crystalline and the resulting residue was followed by filtration and dried to form crystal. Subsequently, the resulting crystal was purified through silica gel column chromatography (developing solvent: chloroform/hexane solvent), thereby obtaining 79.3 g of a triphenylamine derivative compound represented by the general formula (50) (yields: 55.2%).

Workup

  1. additionwere added
  2. temperatureheated for 2 hours
  3. temperatureheated again to 220° C.
  4. customthe reaction for 2.5 hours
  5. temperatureAfter that, the solution was cooled to room temperature
  6. filtrationfollowed by filtration
  7. dissolutionThe resulting residue was dissolved in toluene
  8. customdried over activated clay
  9. dissolutionAfter that, the residue was dissolved in toluene
  10. additionadded with methanol to crystallization
  11. dissolutionThen, the residue was dissolved in toluene again
  12. additionadded with methanol to crystalline and the resulting residue
  13. filtrationwas followed by filtration
  14. customdried
  15. customto form crystal
  16. customSubsequently, the resulting crystal was purified through silica gel column chromatography (developing solvent: chloroform/hexane solvent)

Sources & evidence

ORD record
ord-d092edf406704ca494fd2f9129522dbb
Source dataset
uspto-grants-2008_11
Patent number
US07449602B2

Reaction notes

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