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Potassium Carbonate → HCID 15374911, compound

HRID 1684427
Notes
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Reaction equation

HRID 1684427 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[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]>[C: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]([C:14]([CH3:17])([CH3:16])[CH3:15])=[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)([CH3:17])([CH3:16])[CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 763484,4'-Diiodo-1,1'-biphenylHCID 11447459(4-tert-Butyl-phenyl)-phenyl-amine

Product 1

HCID 15374911HCID 15374911, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

8.1 g (0.036 mol) of N-phenyl-p-tertiarybutylaniline, 7.3 g (0.018 mol) of 4,4'-diiodobiphenyl, 7.5 g (0.054 mol) of anhydrous potassium carbonate, and 0.53 g (0.008 mol) of copper powder were mixed. The mixture was then allowed to undergo reaction at a temperature of 210° to 225° 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: 1/4 mixture of toluene and n-hexane) to obtain 4.5 g (yield: 41.7%) of N,N'-bis(p-tertiarybutylphenyl)-N,N'-diphenylbenzidine. The melting point of the product was from 232.2° C. to 232.6° C.

Workup

  1. customreaction at a temperature of 210° to 225° 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: 1/4 mixture of toluene and n-hexane)

Sources & evidence

ORD record
ord-54a2aa38e5be483daaeb52785e3da51f
Source dataset
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05639914

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes