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N,N'-Diphenyl-P-Phenylenediamine → N1,N1,N4-triphenyl-N4-(4-(phenylamino)phenyl)benzene-1,4-diamine

HRID 716594
Notes
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Reaction equation

HRID 716594 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:22]1[CH:40]=[CH:39][C:25]([N:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:24][CH:23]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:27]1([N:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:25]2[CH:39]=[CH:40][C:22]([N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]3[CH:9]=[CH:10][C:11]([NH:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:12][CH:13]=3)=[CH:23][CH:24]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 6319N,N'-Diphenyl-P-PhenylenediamineHCID 6428384-BromotriphenylamineHCID 23676156Sodium t-butoxide

Product 1

HCID 86718963N1,N1,N4-triphenyl-N4-(4-(phenylamino)phenyl)benzene-1,4-diamineYield 55.6%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalyst
HCID 167845
palladium(II) acetate
Catalyst
HCID 1140TolueneSolvent

Procedure

To a stirred solution of N1,N4-diphenylbenzene-1,4-diamine (6.5 g, 20.0 mmol) in toluene (400 mL), 4-bromo-N,N-diphenylaniline (7.9 g, 30.1 mmol) was added and the solution was degassed with nitrogen for 15 minutes. Palladium (II) acetate (45 mg, 0.2 mmol), triphenylphosphine (210 mg, 0.8 mmol) and sodium tert-butoxide (2.9 g, 30.1 mmol) were added and degassed with nitrogen for another 15 minutes. The reaction was refluxed overnight. The reaction mixture was filtered through Celite®, washed with toluene and the filtrate was concentrated under vacuum. It was then column chromatographed with hexane to 50% toluene/hexane to obtain 5.6 g (48%) of the desired product as a white solid.

Workup

  1. customthe solution was degassed with nitrogen for 15 minutes
  2. customdegassed with nitrogen for another 15 minutes
  3. temperatureThe reaction was refluxed overnight
  4. filtrationThe reaction mixture was filtered through Celite®
  5. washwashed with toluene
  6. concentrationthe filtrate was concentrated under vacuum
  7. customcolumn chromatographed with hexane to 50% toluene/hexane

Sources & evidence

ORD record
ord-bde5c400d61847b99d80e824321ef023
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09190623B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes