Dodecane → N4-(4-Biphenylyl)-N4,N4'-diphenylbiphenyl-4,4'-diamine

HRID 602217Notes

Reaction equation

HRID 602217 reaction equation
IC1C=CC([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14](C(=O)C)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=CC=1.C(=O)([O-])[O-].[K+].[K+].[CH3:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].[OH-].[K+]>C(O)CC(C)C.[Cu].O>[C:36]1([C:35]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:41]=[CH:40][C:39]([N:14]([C:9]2[CH:8]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:15]2[CH:16]=[CH:17][C:18]([C:18]3[CH:19]=[CH:20][C:15]([NH:14][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:8]=4)=[CH:16][CH:17]=3)=[CH:19][CH:20]=2)=[CH:38][CH:37]=1

Participants

8

Reactant 4

HCID 8182DodecaneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 23140821N-(4'-iodobiphenylyl)acetanilide

Product 1

HCID 23140817N4-(4-Biphenylyl)-N4,N4'-diphenylbiphenyl-4,4'-diamineYield 77.8%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 31260Isoamyl AlcoholSolvent

Procedure

There were mixed 16.5 g (0.040 mole) of N-(4′-iodobiphenylyl)acetanilide, 11.8 g (0.048 mole) of N-(4-biphenyl)aniline, 8.3 g (0.060 mole) of anhydrous potassium carbonate, 0.1 g (0.002 mole) of copper powder and 10 ml of n-dodecane, followed by reaction at 200 to 212° C. for 15 hours. The reaction product was extracted with 200 ml of toluene, and the insoluble matter was removed by filtration. Then, the filtrate was concentrated to obtain oily matter. The oily matter was dissolved in 60 ml of isoamyl alcohol, and 4 ml of water and 4.00 g (0.060 mole) of 85% potassium hydroxide were added, followed by hydrolysis at 130° C. After isoamyl alcohol was removed by steam distillation, extraction with 250 ml of toluene was performed, followed by washing with water, drying and concentration. The concentrate was purified by column chromatography (carrier: silica gel, eluate: toluene/n-hexane=1/2) to obtain 15.2 g (yield: 77.8%, HPLC purity: 97.0%) of N-(4-biphenylyl)-N,N′-diphenyl-4,4′-diaminobiphenyl. The melting point was 126.6 to 127.4° C.

Workup

  1. customfollowed by reaction at 200 to 212° C. for 15 hours
  2. extractionThe reaction product was extracted with 200 ml of toluene
  3. customthe insoluble matter was removed by filtration
  4. concentrationThen, the filtrate was concentrated
  5. customto obtain oily matter
  6. customfollowed by hydrolysis at 130° C
  7. customAfter isoamyl alcohol was removed by steam distillation, extraction with 250 ml of toluene
  8. washby washing with water
  9. customdrying
  10. concentrationconcentration
  11. customThe concentrate was purified by column chromatography (carrier: silica gel, eluate: toluene/n-hexane=1/2)

Sources & evidence

ORD record
ord-b304bd8a15b54fc4b7eb2d015d53f486
Source dataset
uspto-grants-2011_03
Patent number
US07902402B2

Reaction notes

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