Ethyl Acetate → N-acetyl-N-(2-methoxyphenyl)-2-phenoxyaniline

HRID 1016590

반응식

HRID 1016590 반응식
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:3])[CH3:2].I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>[N+](C1C=CC=CC=1)([O-])=O.[Cu].[Cu](Br)Br>[C:1]([N:4]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:3])[CH3:2]

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 68257o-IodoanisoleHCID 8970802-Phenoxyacetanilide

생성물 1

HCID 18407187N-acetyl-N-(2-methoxyphenyl)-2-phenoxyaniline

시약·촉매·용매 3

HCID 23978Copper촉매HCID 24611Copper bromide (CuBr2)촉매HCID 7416Nitrobenzene용매

실험 절차

In 20 ml of nitrobenzene were refluxed 2.27 g of N-acetyl-2-phenoxyaniline, 1.3 ml of 2-iodoanisole, 1.38 g of potassium carbonate, 133 mg of a copper powder and 200 mg of copper bromide under heating for 8 hours. The reaction solution was cooled to room temperature, and after addition of ethyl acetate, the insoluble matter was removed by filtration. The filtrate was washed with 0.5 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4) to give 660 mg of N-acetyl-N-(2-methoxyphenyl)-2-phenoxyaniline as an oil.

후처리

  1. temperatureunder heating for 8 hours
  2. customthe insoluble matter was removed by filtration
  3. washThe filtrate was washed with 0.5 N hydrochloric acid
  4. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate
  5. customAfter removal of the drying agent
  6. filtrationby filtration
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4)

출처 및 근거

ORD 기록
ord-1a8967ea92bc4dc6a409e108f220d0fa
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06476056B2

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