Aniline → N4,N4,N4'-Triphenyl-[1,1'-biphenyl]-4,4'-diamine

HRID 31954

Reaction equation

HRID 31954 reaction equation
C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.Br[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([N:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.[NH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(O[Na])(C)(C)C>C1(C)C=CC=CC=1>[C:28]1([N:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:24]2[CH:25]=[CH:26][C:21]([C:18]3[CH:19]=[CH:20][C:15]([NH:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[CH:16][CH:17]=3)=[CH:22][CH:23]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 113155504-Bromo-4'-(diphenylamino)biphenylHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 22013295N4,N4,N4'-Triphenyl-[1,1'-biphenyl]-4,4'-diamineYield 77.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 0.66 weight % toluene solution 100 μl of tri-t-butylphosphine was added to a toluene 100 ml solution of 4-bromo-4′-(N,N-diphenylamino)biphenyl 4.00 g, aniline 1.11 g, tris(benzylideneacetone)-dipalladium (0) 183 mg and t-butoxysodium 1.35 g, and the mixture was stirred at room temperature for 5 hours. After finishing the reaction, the mixture was filtered through celite, and the filtrate was extracted with toluene. This was concentrated under reduced pressure, and the resulting crude product was subjected to column refining to obtain 3.20 g of pale yellow powder of N,N,N′-triphenylbenzidine.

Workup

  1. customthe reaction
  2. filtrationthe mixture was filtered through celite
  3. extractionthe filtrate was extracted with toluene
  4. concentrationThis was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e0f170690ca544d8bc6d4dc7f67f0364
Source dataset
uspto-grants-2008_09
Patent number
US07425654B2

Linked notes

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