2-(Dimethylamino)ethanol → N,N-dimethyl-2-(3-nitro-5-(trifluoromethyl)phenoxy)ethanamine

HRID 1050195노트

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HRID 1050195 반응식
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].F[C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([N+:18]([O-:20])=[O:19])[CH:9]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][O:5][C:8]1[CH:13]=[C:12]([C:14]([F:16])([F:17])[F:15])[CH:11]=[C:10]([N+:18]([O-:20])=[O:19])[CH:9]=1

참가 물질

5

반응물 3

HCID 79022-(Dimethylamino)ethanolHCID 11430Potassium CarbonateHCID 152724001-Fluoro-3-nitro-5-(trifluoromethyl)benzene

생성물 1

HCID 66806497N,N-dimethyl-2-(3-nitro-5-(trifluoromethyl)phenoxy)ethanamine수율 28.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
80 °C

실험 절차

A suspension of 2-(dimethylamino)ethanol (128 mg, 1.435 mmol) in DMF (5 mL) was added to a solution of 1-fluoro-3-nitro-5-(trifluoromethyl)benzene (200 mg, 0.956 mmol) in DMF (5 mL). K2CO3 (264 mg, 1.913 mmol) was added and the mixture was stirred at 80° C. for 8 h. The mixture was cooled to rt. Then the solution was concentrated and distributed between ethyl acetate and saturated NaHCO3 solution. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by preparative TLC (PE/EA=5:1, Rf=0.6) to yield a light yellow solid of N,N-dimethyl-2-(3-nitro-5-(trifluoromethyl)phenoxy)ethanamine (75 mg, 0.270 mmol, 28.2% yield): 1H NMR (400 MHz, CD3OD) δ 8.22-8.02 (m, 2H), 7.72 (s, 1H), 4.43 (t, J=5.1 Hz, 2H), 3.26 (t, J=4.9 Hz, 2H), 2.78-2.60 (m, 6H). ES-LCMS m/z 279 (M+H).

후처리

  1. temperatureThe mixture was cooled to rt
  2. concentrationThen the solution was concentrated
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by preparative TLC (PE/EA=5:1, Rf=0.6)

출처 및 근거

ORD 기록
ord-fef78dfb48ca4085b72eb0b48dafd50a
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382238B2

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