Nitrobenzene → N,N,N',N'-tetra(3-biphenylyl)benzidine

HRID 481933

反応式

HRID 481933 の反応式
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+].[N+:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([O-])=O>[Cu]>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][CH:2]=[C:3]([N:21]([C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=3)[CH:13]=[CH:12][CH:11]=2)[C:24]2[CH:29]=[CH:28][C:27]([C:27]3[CH:28]=[CH:29][C:24]([N:21]([C:10]4[CH:9]=[C:8]([C:5]5[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=5)[CH:13]=[CH:12][CH:11]=4)[C:3]4[CH:4]=[C:5]([C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=5)[CH:6]=[CH:7][CH:2]=4)=[CH:25][CH:26]=3)=[CH:26][CH:25]=2)[CH:4]=1

参加物

5

反応物 3

HCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 763484,4'-Diiodo-1,1'-biphenyl

生成物 1

HCID 22013501N,N,N',N'-tetra(3-biphenylyl)benzidine収率 55.7%

試薬・触媒・溶媒 1

HCID 23978Copper触媒

実験手順

A 500-ml reactor was charged with 44.5 g (0.139 mol) of di(3-biphenyl)amine, 27.6 g (0.0680 mol) of 4,4'-diiodobiphenyl, 34.3 g (0.249 mol) of potassium carbonate, 2.3 g of copper powder, and 180 ml of nitrobenzene. In an argon stream, the contents were heated under reflux for 24 hours. At the end of reaction, the insoluble was removed by filtration and the filtrate was distilled of the solvent. The still residue was purified through a silica gel column with a 3/1 mixture of n-hexane and toluene, obtaining 30 g of N,N,N',N'-tetra(3-biphenylyl)benzidine of primary purity grade (yield 55.7%). It was further purified by recrystallization from toluene, obtaining 6.0 g of a 99.58% pure fraction and 5.0 g of a 99.23% pure fraction (combined yield 20.496). Further purification by sublimation yielded 8.0 g of a 99.99% pure product.

後処理

  1. temperatureIn an argon stream, the contents were heated
  2. temperatureunder reflux for 24 hours
  3. customAt the end of reaction
  4. customthe insoluble was removed by filtration
  5. distillationthe filtrate was distilled of the solvent
  6. customThe still residue was purified through a silica gel column with a 3/1 mixture of n-hexane and toluene

出典と根拠

ORDレコード
ord-ac37574bc2a1464ca3e20107cedb7833
出典データセット
uspto-grants-1998_08
特許番号
US05792557

関連ノート

読み込み中…