Nitrobenzene → 4'-ethyl-N-(4'-methoxy-[1,1'-biphenyl]-4-yl)-N-(4-methylphenyl)-[1,1'-biphenyl]-4-amine

HRID 52816노트

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HRID 52816 반응식
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[CH3:2].[N+]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([O-])=O.[C:32](=[O:35])([O-])[O-].[K+].[K+]>C1CCCCC1.C1(C)C=CC=CC=1.[Cu]>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]([C:29]3[CH:30]=[CH:31][C:26]([C:3]4[CH:8]=[CH:7][C:6]([O:35][CH3:32])=[CH:5][CH:4]=4)=[CH:27][CH:28]=3)[C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)[CH3:2]

참가 물질

7

반응물 3

HCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 199639404'-ethyl-N-(4-methylphenyl)-[1,1'-biphenyl]-4-amine

생성물 1

HCID 151001124'-ethyl-N-(4'-methoxy-[1,1'-biphenyl]-4-yl)-N-(4-methylphenyl)-[1,1'-biphenyl]-4-amine

시약·촉매·용매 3

HCID 23978Copper촉매HCID 1140Toluene용매HCID 8078Cyclohexane용매

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온도
210 °C

실험 절차

To 4.31 g (15.0 mmol) of the thus obtained 4'-ethyl-N-(4-methylphenyl) -[1,1'-biphenyl]-4-amine were added 60 ml of nitrobenzene, 5.58 g (18.0 mmol) of 4'-iodine-4'-methoxy-[1,1'-biphenyl], 4.15 g of potassium carbonate, and 0.48 g of copper powder. The mixture was placed in an ester pipe and azeotropically heated for dehydration, with stirring, at 210° C. for 11 hours as a nitrogen gas was caused to flow over the mixture. The reaction mixture was then cooled to room temperature and filtered through a Celite filter to obtain a filtrate. The nitrobenzene was distilled away from the filtrate under reduced pressure. The residue was extracted with toluene, washed with water, dried by use of magnesium sulfate, and condensed under reduced pressure, whereby orange brown crystals were obtained. The thus obtained product was subjected to a silica gel column chromatography by use of a mixed solvent of cyclohexane and toluene as an eluent, and recrystallized from a mixed solvent of ethanol and toluene, whereby 4'-ethyl-N-(4'-methoxy-[1,1'-biphenyl]-4-yl)-N-(4-methylphenyl)-[1,1'-biphenyl]-4-amine (Aminobiphenyl Compound No. 2-62 in Table 3) was obtained in the form of colorless needles with a yield of 4.00 g (56.8%). The melting point of the product was 159.5° C. to 161.5° C.

후처리

  1. temperatureazeotropically heated for dehydration
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. filtrationfiltered through a Celite
  4. filtrationfilter
  5. customto obtain a filtrate
  6. distillationThe nitrobenzene was distilled away from the filtrate under reduced pressure
  7. extractionThe residue was extracted with toluene
  8. washwashed with water
  9. dry with materialdried by use of magnesium sulfate, and condensed under reduced pressure, whereby orange brown crystals
  10. customwere obtained
  11. customrecrystallized from a mixed solvent of ethanol and toluene

출처 및 근거

ORD 기록
ord-3f160b61d77544ccad66fe5ed850a087
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616801

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