Potassium Carbonate → HCID 19708501, compound

HRID 725733Notes

Reaction equation

HRID 725733 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28](I)=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]>[CH2:14]([C:11]1[CH:10]=[CH:9][C:8]([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([N:7]([C:8]4[CH:9]=[CH:10][C:11]([CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:12][CH:13]=4)[C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)[CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 763484,4'-Diiodo-1,1'-biphenylHCID 19708500HCID 19708500, compound

Product 1

HCID 19708501HCID 19708501, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

17.6 g (0.078 mol) of N-phenyl-p-isobutylaniline, 12.6 g (0.031 mol) of 4,4'-diiodobiphenyl, 12.9 g (0.093 mol) of anhydrous potassium carbonate, and 0.89 g (0.014 mol) of copper powder were mixed. The mixture was then allowed to undergo reaction at a temperature of 190° to 220° C. for 12 hours. The reaction product was then extracted with 70 ml of toluene. The insoluble contents were removed by filtration. The filtrate was then concentrated to obtain an oily material. The crude product thus obtained was then purified by column chromatography (carrier: silica gel; elute: 1/6 mixture of toluene and n-hexane) to obtain 8.5 g (yield: 45.7%) of N,N'-bis(p-isobutylphenyl)-N,N'-diphenylbenzidine. The melting point of the product was from 133.8° C. to 135.3° C.

Workup

  1. customreaction at a temperature of 190° to 220° C. for 12 hours
  2. extractionThe reaction product was then extracted with 70 ml of toluene
  3. customThe insoluble contents were removed by filtration
  4. concentrationThe filtrate was then concentrated
  5. customto obtain an oily material
  6. customThe crude product thus obtained
  7. customwas then purified by column chromatography (carrier: silica gel; elute: 1/6 mixture of toluene and n-hexane)

Sources & evidence

ORD record
ord-70c7a09973e04d0dabe5fc3e682d3bf3
Source dataset
uspto-grants-1998_01
Patent number
US05707747

Reaction notes

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