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Dodecane → N,N'-di(4-methoxy-2-methylphenyl)-N,N'-diphenyl-4,4''-diamino-p-terphenyl

HRID 2356190
Notes
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Reaction equation

HRID 2356190 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:5]([CH3:16])[CH:4]=1.I[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][C:33](I)=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)=[CH:20][CH:19]=1.[C:37](=[O:40])([O-])[O-].[K+].[K+].CCCCC[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54]>[Cu]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][C:33]([N:9]([C:54]5[CH:53]=[CH:52][C:51]([O:40][CH3:37])=[CH:50][C:49]=5[CH3:48])[C:6]5[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=5)=[CH:32][CH:31]=4)=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)=[C:5]([CH3:16])[CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8182DodecaneHCID 11430Potassium CarbonateHCID 1624614-methoxy-2-methyl-N-phenylanilineHCID 35635834,4''-Diiodo-p-terphenyl

Product 1

HCID 59456699N,N'-di(4-methoxy-2-methylphenyl)-N,N'-diphenyl-4,4''-diamino-p-terphenylYield 80%

Reagents, catalysts & solvents 1

HCID 23978
Copper
Catalyst

Conditions

Temperature
205 °C

Procedure

(4-Methoxy-2-methylphenyl)phenylamine (14.1 g (0.066 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=1:2) to obtain 15.7 g of N,N′-di(4-methoxy-2-methylphenyl)-N,N′-diphenyl-4,4″-diamino-p-terphenyl (compound No. 2) (yield: 80.0%, melting point: 180.8 to 183.4° 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=1:2)

Sources & evidence

ORD record
ord-9627b82b458248329c6b4fd166012d48
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07759030B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes