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

HRID 1819731

Reaktionsgleichung

Reaktionsgleichung von HRID 1819731
[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

Komponenten

6

Edukt 4

HCID 176Acetic Acid3×HCID 1140TolueneHCID 99644-(Trifluoromethyl)anilineHCID 121699Methyl 3-oxovalerate

Produkt 1

HCID 68545758Methyl 3-(4-trifluoromethylphenylamino)-2-pentenoateAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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%.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a5b7a54b457948e4a9b314aabba51ac7
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601842B2

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