Diethyl Ether → N-[4-chloro-2-fluoro-5-(1-methoxyethyl)phenyl]acetamide

HRID 231425ノート

反応式

HRID 231425 の反応式
[N+]([O-])([O:3][CH:4]([C:6]1[CH:11]=[C:10]([NH:12][C:13]([CH3:15])=[O:14])[C:9]([F:16])=[CH:8][C:7]=1[Cl:17])[CH3:5])=O.C[O-].[Na+].[CH2:22](OCC)C>CO>[Cl:17][C:7]1[C:6]([CH:4]([O:3][CH3:22])[CH3:5])=[CH:11][C:10]([NH:12][C:13](=[O:14])[CH3:15])=[C:9]([F:16])[CH:8]=1

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 10942334Sodium Methoxide2 回HCID 145018071-(2-Chloro-4-fluoro-5-methylcarbonylaminophenyl)ethyl nitrate

生成物 1

HCID 14501808N-[4-chloro-2-fluoro-5-(1-methoxyethyl)phenyl]acetamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a clear, colorless solution of 0.4 g (0.0015 mole) of 1-(2-chloro-4-fluoro-5-methylcarbonylaminophenyl)ethyl nitrate in 15 ml of absolute methanol was added dropwise 0.31 g (0.0015 mole) of a 25 weight percent solution of sodium methoxide in methanol. The reaction mixture turned pale yellow immediately and was stirred at room temperature for 2.5 hours. An additional 0.31 g (0.0015 mole) of the sodium methoxide solution was added, and stirring at room temperature continued for 18 hours. The mixture was heated at reflux for 2.5 hours and then was allowed to cool to room temperature. To the mixture was added 100 ml of diethyl ether, and this mixture was washed with water. The diethyl ether solution was dried, filtered, and the solvent was evaporated under reduced pressure, yielding 0.28 g of N-[4-chloro-2-fluoro-5-(1-methoxyethyl)phenyl]acetamide. The nmr and ir spectra were consistent with the proposed structure. This reaction was repeated to provide sufficient starting material for Step G.

後処理

  1. stirringstirring at room temperature
  2. waitcontinued for 18 hours
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 2.5 hours
  5. temperatureto cool to room temperature
  6. washthis mixture was washed with water
  7. dry with materialThe diethyl ether solution was dried
  8. filtrationfiltered
  9. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-89a09a998bbf47828e7dbdc9e758b2a0
出典データセット
uspto-grants-1989_07
特許番号
US04846882

反応ノート

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