Dodecane → N,N'-diphenyl-N,N'-di-p-tolyl-4,4''-diamino-p-terphenyl

HRID 2356191Notes

Reaction equation

HRID 2356191 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][C:31](I)=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CCCCC[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]>[Cu]>[C:1]1([N:7]([C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=2)[C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][C:31]([N:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[C:50]5[CH:49]=[CH:48][C:47]([CH3:46])=[CH:52][CH:51]=5)=[CH:30][CH:29]=4)=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8182DodecaneHCID 11430Potassium CarbonateHCID 12109N-Phenyl-p-toluidineHCID 35635834,4''-Diiodo-p-terphenyl

Product 1

HCID 14008244N,N'-diphenyl-N,N'-di-p-tolyl-4,4''-diamino-p-terphenylYield 76.4%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
205 °C

Procedure

Phenyl-p-tolylamine (11.5 g (0.063 mol)), 14.5 g (0.030 mol) of 4,4″-diiodo-p-terphenyl, 5.0 g (0.036 mol) of anhydrous potassium carbonate, 0.38 g (0.006 mol) of copper powder and 15 ml of n-dodecane were mixed, and heated up to 200 to 210° C. while introducing nitrogen gas, followed by stirring for 30 hours. After the termination of the reaction, the reaction product was extracted with 400 ml of toluene, and insoluble matter was removed by filtration. Then, the filtrate was concentrated to dryness. The resulting solid matter was purified by column chromatography (carrier: silica gel, eluent: toluene:hexane=1:4) to obtain 13.6 g of N,N′-diphenyl-N,N′-di-p-tolyl-4,4″-diamino-p-terphenyl (compound No. 17) (yield: 76.4%, melting point: 167.2 to 168.2° C.).

Workup

  1. additionwhile introducing nitrogen gas
  2. customAfter the termination of the reaction
  3. extractionthe reaction product was extracted with 400 ml of toluene, and insoluble matter
  4. customwas removed by filtration
  5. concentrationThen, the filtrate was concentrated to dryness
  6. customThe resulting solid matter was purified by column chromatography (carrier: silica gel, eluent: toluene:hexane=1:4)

Sources & evidence

ORD record
ord-2f947d001eb3442abda9f12d95a7bfeb
Source dataset
uspto-grants-2010_07
Patent number
US07759030B2

Reaction notes

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