Aniline → N,N,N'-triphenyl-4-phenylenediamine

HRID 31955

Reaction equation

HRID 31955 reaction equation
C(P([C:10]([CH3:13])([CH3:12])C)C(C)(C)C)(C)(C)C.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:21](O[Na])([CH3:24])([CH3:23])C>C1(C)C=CC=CC=1>[C:15]1([N:14]([C:12]2[CH:10]=[CH:13][CH:23]=[CH:21][CH:24]=2)[C:18]2[CH:19]=[CH:20][C:15]([NH:14][C:23]3[CH:21]=[CH:24][CH:13]=[CH:10][CH:12]=3)=[CH:16][CH:17]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 161288N,N,N'-triphenyl-4-phenylenediamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 0.66 weight % toluene solution 150 μl of tri-t-butylphosphine was added to a toluene 50 ml solution of 4-bromo-triphenylamine 5.00 g, aniline 1.72 g, tris(benzylideneacetone)dipalladium (0) 282 mg and t-butoxysodium 2.07 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 4.20 g of pale yellow powder of N,N,N′-triphenyl-1,4-phenylenediamine.

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-4632e024989c4ccd8583294dd7a8a054
Source dataset
uspto-grants-2008_09
Patent number
US07425654B2

Linked notes

Loading…