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

HRID 1016590

反応式

HRID 1016590 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23978Copper触媒HCID 24611Copper bromide (CuBr2)触媒HCID 7416Nitrobenzene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1a8967ea92bc4dc6a409e108f220d0fa
出典データセット
uspto-grants-2002_11
特許番号
US06476056B2

関連ノート

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