Toluene → 4-(acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole

HRID 352073

Reaktionsgleichung

Reaktionsgleichung von HRID 352073
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1.ClCC(CCl)=O.[C:22]1([CH3:28])[CH:27]=CC=CC=1.[C:29]([O-:32])(=[O:31])[CH3:30].[Na+]>CO.CS(C)=O>[C:29]([O:32][CH2:28][C:22]1[N:13]=[C:11](/[CH:10]=[CH:9]/[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:14])([F:15])[F:1])=[CH:8][CH:7]=2)[O:12][CH:27]=1)(=[O:31])[CH3:30]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 107931,3-DichloroacetoneHCID 517045Sodium AcetateHCID 57090144-(Trifluoromethyl)cinnamamide

Produkt 1

HCID 129928464-(acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazoleAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

(E)-3-(4-(Trifluoromethyl)phenyl)-2-propenamide (950 g, 4.42 mol) and 1,3-dichloroacetone (1045 g, 8.23 mol)were added to toluene (4.75 L) and the mixture was subjected to refluxing azeotropic dehydration using a Dean-Stark tube for 8 hours. During the reaction, an azeotropic mixture (2.38 L) was removed. The reaction mixture was concentrated under reduced pressure, and dimethyl sulfoxide (4.75L) and sodium acetate (905 g, 11.0 mol) were added to the residue. The mixture was stirred at 70-80° C. for 3.5 hours. Methanol (4.75 L) was added. After allowing to cool to room temperature and stirring, the mixture was stirred for 1 hour under ice-cooling. The precipitated crystals were collected by filtration, washed with cold-methanol (1.9 L), and dried under reduced pressure to give 4-(acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole (1560 g, yield 51%).

Aufarbeitung

  1. temperatureto refluxing azeotropic dehydration
  2. customfor 8 hours
  3. customDuring the reaction
  4. customan azeotropic mixture (2.38 L) was removed
  5. additionwere added to the residue
  6. temperatureto cool to room temperature
  7. stirringstirring
  8. stirringthe mixture was stirred for 1 hour under ice-
  9. temperaturecooling
  10. filtrationThe precipitated crystals were collected by filtration
  11. washwashed with cold-methanol (1.9 L)
  12. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-87acf2d9cbc24512b9fdde5a0a549b33
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743924B2

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