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

HRID 1953

반응식

HRID 1953 반응식
[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

참가 물질

7

반응물 4

HCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 196889145-[N-(4-tolyl)amino]acenaphthene2회

생성물 1

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

시약·촉매·용매 2

HCID 23978Copper촉매HCID 1140Toluene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a22b523213134b988e3fb268968dfa76
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728500

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