Nitrobenzene → 5-[N-(4-tolyl)-N-phenylamino]acenaphthene

HRID 1953

反応式

HRID 1953 の反応式
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:18]3[C:19]4[C:11]([CH2:12][CH2:13][C:14]=4[CH:15]=[CH:16][CH:17]=3)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.I[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[N+](C1C=CC=CC=1)([O-])=O>[Cu].C1(C)C=CC=CC=1>[C:1]1([CH3:20])[CH:2]=[CH:3][C:4]([N:7]([C:8]2[C:18]3[C:19]4[C:11]([CH2:12][CH2:13][C:14]=4[CH:15]=[CH:16][CH:17]=3)=[CH:10][CH:9]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:5][CH:6]=1

参加物

7

反応物 4

HCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 196889145-[N-(4-tolyl)amino]acenaphthene2 回

生成物 1

HCID 196889135-[N-(4-tolyl)-N-phenylamino]acenaphthene収率 83.8%

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 1140Toluene溶媒

実験手順

4.66 g (0.018 mol) of the above prepared 5-[N-(4-tolyl)amino]acenaphthene was mixed with 4.99 g (0.022 mol) of iodo benzene, 0.13 g (0.002 mol) of copper powder, 2.76 g (0.02 mol) of anhydrous potassium carbonate and 5 ml of nitrobenzene, and the resultant mixture was stirred at 200° C. for 25 hours. The reaction was determined to be finished when disappearance of 5-[N-(4-tolyl)amino]acenaphthene was identified. 100 ml of toluene was added thereto to dissolve the reaction product, and the mixture was filtrated and concentrated. The concentrated material thus obtained was purified by column chromatography (carrier: silica gel, eluent: toluene/hexane=1/4) to obtain 5.06 g (yield: 83.8%, melting point: 147.0°-148.0° C.) of 5-[N-(4-tolyl)-N-phenylamino]acenaphthene.

後処理

  1. dissolutionto dissolve the reaction product
  2. filtrationthe mixture was filtrated
  3. concentrationconcentrated
  4. customThe concentrated material thus obtained
  5. customwas purified by column chromatography (carrier: silica gel, eluent: toluene/hexane=1/4)

出典と根拠

ORDレコード
ord-a22b523213134b988e3fb268968dfa76
出典データセット
uspto-grants-1998_03
特許番号
US05728500

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