Dimethylformamide → N~4~,N~4'~-Di(naphthalen-2-yl)-N~4~,N~4'~-diphenyl(1,1'-biphenyl)-4,4'-diamine

HRID 1816861Notes

Reaction equation

HRID 1816861 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:21]1([NH:27][C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:38][N:39]([CH:41]=O)C>[Cu].O>[CH:24]1[CH:25]=[CH:26][C:21]([N:27]([C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=2)[C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([N:39]([C:41]4[CH:32]=[CH:31][C:30]5[C:35](=[CH:36][CH:37]=[CH:28][CH:29]=5)[CH:34]=4)[C:38]4[CH:23]=[CH:22][CH:21]=[CH:26][CH:25]=4)=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8679N-phenyl-2-naphthylamineHCID 11430Potassium CarbonateHCID 763484,4'-Diiodo-1,1'-biphenyl

Product 1

HCID 21881245N~4~,N~4'~-Di(naphthalen-2-yl)-N~4~,N~4'~-diphenyl(1,1'-biphenyl)-4,4'-diamineYield 72.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

25.1 g (61.5 mmol) of 4,4′-diiodobiphenyl, 2.14 g of poly(ethylene glycol) PEG-6000 that was available from Wako Pure Chemical Industries, Ltd., 17.1 g (0.124 mol) of potassium carbonate and 15.7 g (247 mmol) of powdered copper were added to 32.4 g (148 mmol) of N-phenyl-2-naphthylamine. It was heated at 200 degrees Centigrade. It was determined for tracing by the high-speed liquid chromatography. And it was stirred and refluxed for 12 hours until no peaks of starting materials and intermediates were determined. DMF and water were added thereto to disperse. It was filtrated and washed with water. Precipitated crystals were purified by silica gel column chromatography to obtain 26.2 g of beta-NPD that is represented by Compound Example 5 at 72.4% yield.

Workup

  1. temperatureIt was heated at 200 degrees Centigrade
  2. temperaturerefluxed for 12 hours until no peaks of starting materials and intermediates
  3. additionto disperse
  4. filtrationIt was filtrated
  5. washwashed with water
  6. customPrecipitated crystals
  7. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d21b99ba0051478fab22b87c296849b2
Source dataset
uspto-grants-2009_10
Patent number
US07598010B2

Reaction notes

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