Nitrogen → 2-(2-Dimethylaminoethoxy)-4-nitroanisole

HRID 900465노트

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HRID 900465 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[OH:12].Cl.Cl[CH2:15][CH2:16][N:17]([CH3:19])[CH3:18].[H-].[Na+].N#N>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[O:12][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18]

참가 물질

6

반응물 4

HCID 947NitrogenHCID 24758Sodium hydrideHCID 694712-Methoxy-5-nitrophenolHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

생성물 1

HCID 107764242-(2-Dimethylaminoethoxy)-4-nitroanisole수율 65%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

To a solution of 2-methoxy-5-nitro-phenol (10 g), (2-chloroethyl)-dimethyl-amine hydrochloride (9.37 g) in dimethylformamide (150 mL) was added NaH (2.98 g) slowly under N2 and at room temperature. The mixture was then stirred at 140° C. heating with an oil bath for 5 hours. The reaction was concentrated to dryness, dissolved in 2 M HCl (200 mL) and washed with ethyl acetate (2×100 mL). The aqueous layer was basified with K2CO3, extracted with dichloromethane (3×200 mL) and ethyl acetate (2×100 mL), dried over Na2SO4, filtered, concentrated to give [2-(2-Methoxy-5-nitro-phenoxy)-ethyl]-dimethylamine (9.17 g, 65% yield). LCMS (m/z) M+H, 241.1.

후처리

  1. customat room temperature
  2. temperatureheating with an oil bath for 5 hours
  3. concentrationThe reaction was concentrated to dryness
  4. dissolutiondissolved in 2 M HCl (200 mL)
  5. washwashed with ethyl acetate (2×100 mL)
  6. extractionextracted with dichloromethane (3×200 mL) and ethyl acetate (2×100 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ecc98e2283ab49c2a4c5e8736017ecea
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07358370B2

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