2-Chlorobenzyl chloride → N-acetyl-N-(2-chlorobenzyl)-2-phenoxyaniline

HRID 1016569

반응식

HRID 1016569 반응식
[H-].[Na+].[C:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:5])[CH3:4].[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Cl>CN(C)C=O>[C:3]([N:6]([CH2:23][C:22]1[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=1[Cl:20])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:5])[CH3:4]

참가 물질

5

반응물 3

HCID 119062-Chlorobenzyl chlorideHCID 24758Sodium hydrideHCID 8970802-Phenoxyacetanilide

생성물 1

HCID 18407206N-acetyl-N-(2-chlorobenzyl)-2-phenoxyaniline수율 94.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 400 mg of sodium hydride (60% in oil) in 30 ml of dimethylformamide was added 2.00 g of N-acetyl-2-phenoxyaniline at room temperature, followed by stirring at room temperature for 30 minutes. To the solution was added dropwise 1.64 g of 2-chlorobenzyl chloride at room temperature with stirring, followed by stirring for 30 minutes. After addition of ice-water, the reaction mixture was extracted with ether. The extract 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 2.92 g of N-acetyl-N-(2-chlorobenzyl)-2-phenoxyaniline as an oil.

후처리

  1. stirringwith stirring
  2. stirringby stirring for 30 minutes
  3. extractionthe reaction mixture was extracted with ether
  4. washThe extract was washed with 0.5 N hydrochloric acid
  5. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate
  6. customAfter removal of the drying agent
  7. filtrationby filtration
  8. concentrationthe solvent was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4)

출처 및 근거

ORD 기록
ord-74ec7bab891f46928df49dd550016812
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06476056B2

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