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

HRID 716594

Reaktionsgleichung

Reaktionsgleichung von HRID 716594
[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

Komponenten

7

Edukt 3

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

Produkt 1

HCID 86718963N1,N1,N4-triphenyl-N4-(4-(phenylamino)phenyl)benzene-1,4-diamineAusbeute 55,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11776TriphenylphosphineKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bde5c400d61847b99d80e824321ef023
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09190623B2

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