Aniline → N-Phenyl-3,5-diphenylaniline

HRID 2273807

Reaction equation

HRID 2273807 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(O[Na])(C)(C)C>C1(C)C=CC=CC=1.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:2]1([NH:1][C:18]2[CH:17]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:15]=[C:14]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:19]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 7076M-TerphenylHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 58672307N-Phenyl-3,5-diphenylanilineYield 84%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Aniline (3 g, 10.75 mmol), m-terphenyl (3.34 g, 10.85 mmol), Pd2(dba)3 (3 mol %), and t-BuONa (1.45 g, 15.05 mmol) is dissolved in toluene in a round flask, and a solution thereof is stirred at 100° C. Upon finishing reaction thereof, the toluene is removed from the solution, and a compound is extracted from the solution by using water and dichloromethane. The compound extracted thus is separated by using silica gel. The separated substance is re-crystallized by using dichloromethane and petroleum ether, and filtered, to obtain N-Phenyl-3,5-diphenylaniline (2.9 g, 84%).

Workup

  1. customreaction
  2. customthe toluene is removed from the solution
  3. extractiona compound is extracted from the solution
  4. extractionThe compound extracted thus
  5. customis separated
  6. customThe separated substance is re-crystallized
  7. filtrationfiltered

Sources & evidence

ORD record
ord-194b2c20ee57495199acfe6705fd3513
Source dataset
uspto-grants-2015_09
Patent number
US09126892B2

Linked notes

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