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

HRID 511877

반응식

HRID 511877 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 11.2 g (500 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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c4b5c490692b4e868d568661cde3fb07
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09101614B2

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