Acetic Acid → Methyl 3-(4-trifluoromethylphenylamino)-2-pentenoate

HRID 1819731

반응식

HRID 1819731 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.C(O)(=O)C>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 4

HCID 176Acetic Acid3회HCID 1140TolueneHCID 99644-(Trifluoromethyl)anilineHCID 121699Methyl 3-oxovalerate

생성물 1

HCID 68545758Methyl 3-(4-trifluoromethylphenylamino)-2-pentenoate수율 72.8%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

In a 1 L-flask were placed 4-trifluoromethylaniline (161 g, 1.00 mol), methyl 3-oxopentanoate (130 g, 1.00 mol) and toluene (160 mL). To this solution was added acetic acid (16 g, 0.27 mol), and the resulting mixture was heated in a bath kept at 100° C. under a reduced pressure of 19 kPa for 3.5 hours, while the water generated was taken out of the reaction system by using a Dean-Stark trap under reflux. Acetic acid (16 g, 0.27 mol) was then added, and reflux was continued for 4.5 hours. Acetic acid (8 g, 0.13 mol) was then added again, and reflux was continued for another 2.5 hours. The heating was then discontinued, nitrogen leaked in, and the reaction mixture cooled. After distillation of the solvent and acetic acid under reduced pressure, the residue was distilled under reduced pressure to give 199 g of the title compound. The yield was 72.8%.

후처리

  1. temperaturethe resulting mixture was heated in a bath
  2. temperatureunder reflux
  3. temperaturereflux
  4. temperaturereflux
  5. waitwas continued for another 2.5 hours
  6. temperaturecooled
  7. distillationAfter distillation of the solvent and acetic acid under reduced pressure
  8. distillationthe residue was distilled under reduced pressure

출처 및 근거

ORD 기록
ord-a5b7a54b457948e4a9b314aabba51ac7
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601842B2

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