Toluene → Methyl 3-(4-trifluoromethylphenylamino)-2-pentenoate

HRID 1931782

반응식

HRID 1931782 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.O=[C:13]([CH2:19][CH3:20])[CH2:14][C:15]([O:17][CH3:18])=[O:16].C1(C)C=CC=CC=1>B(F)(F)F.CCOCC.O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:13]([CH2:19][CH3:20])=[CH:14][C:15]([O:17][CH3:18])=[O:16])=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 1140TolueneHCID 99644-(Trifluoromethyl)anilineHCID 121699Methyl 3-oxovalerate

생성물 1

HCID 68545758Methyl 3-(4-trifluoromethylphenylamino)-2-pentenoate수율 77.1%

시약·촉매·용매 2

HCID 8000Boron trifluoride etherate촉매HCID 962Water용매

실험 절차

In a 500-ml flask, 4-trifluoromethylaniline (80.6 g, 0.5 mol), methyl 3-oxopentanoate (65.1 g, 0.5 mol) and toluene 400 ml were placed. To this solution was added boron trifluoride etherate (1.42 g, 10 mmol), and the resulting mixture was heated under a reduced pressure of 8 kPa. The reaction mixture was heated for 5 hours under reflux, while water produced was removed out of the reaction system by using a Dean-Stark trap. Then, the heating was discontinued and nitrogen was leaked. After cooling, the solvent was removed by distillation by using a rotary evaporator. The residue was then distilled under reduced pressure to give 105.3 g of the title compound. The yield was 77.1%.

후처리

  1. temperaturethe resulting mixture was heated under a reduced pressure of 8 kPa
  2. temperatureThe reaction mixture was heated for 5 hours
  3. customproduced
  4. customwas removed out of the reaction system
  5. temperatureAfter cooling
  6. customthe solvent was removed by distillation
  7. customa rotary evaporator
  8. distillationThe residue was then distilled under reduced pressure

출처 및 근거

ORD 기록
ord-0d61cdd8d0244f4184f8046bebc76fc4
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188307B2

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