Methyl iodide → N-(2-Methoxy-5-nitro-phenyl)-N-methyl-propionamide

HRID 240918

反応式

HRID 240918 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[NH:12][C:13](=[O:16])[CH2:14][CH3:15].[H-].[Na+].I[CH3:20]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]([CH3:20])[C:13](=[O:16])[CH2:14][CH3:15]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2176144N-(2-methoxy-5-nitrophenyl)propanamide

生成物 1

HCID 59167877N-(2-Methoxy-5-nitro-phenyl)-N-methyl-propionamide収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 11.2 g (50.0 mmol) of (2) in 150 mL of anhydrous THF at 0° C. under the nitrogen, was added 3.0 g (75 mmol) of NaH (60% in oil). The suspension was stirred for 0.5 h at 0° C. and 10 mL (150 mmol) of iodomethane was added at 0° C. After the mixture warmed to room temperature and stirred for 3 h, the reaction was quenched by ice brine and extracted with EtOAc (200 mL). The organic phase was washed with brine, dried (Na2SO4), filtered, evaporated in vacuo and the solid was washed with hexane/EtOAc (9:1) to give pure product N-(2-Methoxy-5-nitro-phenyl)-N-methyl-propionamide (3) as a light yellow solid (11.3 g, 95% yield).

後処理

  1. temperatureAfter the mixture warmed to room temperature
  2. stirringstirred for 3 h
  3. customthe reaction was quenched by ice brine
  4. extractionextracted with EtOAc (200 mL)
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. washthe solid was washed with hexane/EtOAc (9:1)

出典と根拠

ORDレコード
ord-59ff6f68e6c443fbba72cf7dcb37dadf
出典データセット
uspto-grants-2014_02
特許番号
US08648104B2

関連ノート

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