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

HRID 1016569

反応式

HRID 1016569 の反応式
[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]

参加物

5

反応物 3

HCID 119062-Chlorobenzyl chlorideHCID 24758Sodium hydrideHCID 8970802-Phenoxyacetanilide

生成物 1

HCID 18407206N-acetyl-N-(2-chlorobenzyl)-2-phenoxyaniline収率 94.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-74ec7bab891f46928df49dd550016812
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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