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

HRID 1050195ノート

反応式

HRID 1050195 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fef78dfb48ca4085b72eb0b48dafd50a
出典データセット
uspto-grants-2016_07
特許番号
US09382238B2

反応ノート

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