Pyrrolidine → E-1-(1-pyrrolidinyl)-2-[2-nitro-4-(4-fluorophenoxy)phenyl]ethylene

HRID 263437

반응식

HRID 263437 반응식
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[CH3:18])([O-:3])=[O:2].CO[CH:21](OC)[N:22]([CH3:24])[CH3:23].N1CC[CH2:29][CH2:28]1>CN(C)C=O>[N:22]1(/[CH:24]=[CH:18]/[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:23][CH2:29][CH2:28][CH2:21]1

참가 물질

5

반응물 3

HCID 31268PyrrolidineHCID 78373Dimethylformamide dimethyl acetalHCID 35376734-(4-Fluorophenoxy)-1-methyl-2-nitrobenzene

생성물 1

HCID 19038053E-1-(1-pyrrolidinyl)-2-[2-nitro-4-(4-fluorophenoxy)phenyl]ethylene수율 103.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

2-Nitro-4-(4-fluorophenoxy)toluene (11.8 g, 47.7 mmol), was dissolved in dimethylformamide (90.0 mL) under N2 atmosphere. Dimethylformamide dimethyl acetal (20.2 mL, 143 mmol), and pyrrolidine (4.0 mL, 47.4 mmol) were added via syringe and the reaction mixture was heated at 110° C. for 3 hours. The reaction mixture was cooled to ambient temperature and partitioned between H2O and ether. The organic phase was washed with H2O. The combined aqueous extracts were washed with ether. The ether extracts were combined and dried over Na2SO4, filtered, and concentrated in vacuo to give a viscous oil (16.1 g) which was used without further purification.

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. custompartitioned between H2O and ether
  3. washThe organic phase was washed with H2O
  4. washThe combined aqueous extracts were washed with ether
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-91ad2b0cc9b648a99f036c8dce7d451b
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05643922

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