Aniline → N,N'-diphenyl-N-1-naphthylbenzidine

HRID 751747

Reaction equation

HRID 751747 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[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[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.[NH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C(O[Na])(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(C)C=CC=CC=1>[C:28]1([N:27]([C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[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:44][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[CH:16][CH:17]=3)=[CH:22][CH:23]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 16755312N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amineHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 22253844N,N'-diphenyl-N-1-naphthylbenzidineYield 75.7%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent2×

Procedure

Adding 0.66% by weight toluene solution in an amount of 100 microliter prepared by dissolving tri-t-butylphosphine into a mixed solution prepared by dissolving 4.50 g of 4-bromo-4′-(N-1-naphthyl-N-phenylamino)biphenyl, 1.11 g of aniline, 183 milligram of tris(dibenzylideneacetone)dipalladium(O) and 1.35 g of t-butoxysodium into toluene in an amount of 100 milliliter, the resultant solution was stirred at a room temperature for 5 hours. After the completion of the reaction, the solution was filtered with a use of celite and the filtrate was extracted with toluene. Concentrating the filtrate under a reduced pressure, the resultant crude product was refined by means of a column and as a result, 3.50 g of pale yellow powder was obtained

Workup

  1. customprepared
  2. customprepared
  3. customAfter the completion of the reaction
  4. filtrationthe solution was filtered with a use of celite
  5. extractionthe filtrate was extracted with toluene
  6. concentrationConcentrating the filtrate under a reduced pressure

Sources & evidence

ORD record
ord-2762be378194415ea1133e43088929d1
Source dataset
uspto-grants-2008_07
Patent number
US07405326B2

Linked notes

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