Ammonia → 4-(Trifluoromethyl)-cinnamamide

HRID 352053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 352053
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9](O)=[O:10])=[CH:5][CH:4]=1.C1(C)C=CC=CC=1.S(Cl)(Cl)=O.[NH3:27]>CN(C)C=O>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([NH2:27])=[O:10])=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 1140TolueneHCID 24386Thionyl ChlorideHCID 749403-[4-(Trifluoromethyl)phenyl]prop-2-enoic acid

Produkt 1

HCID 27790124-(Trifluoromethyl)-cinnamamideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

4-(Trifluoromethyl)cinnamic acid (64.85 g, 300 mmol) was added to toluene (325 ml) and dimethylformamide (2.2 ml). Thionyl chloride (26.3 ml, 361 mmol) was added dropwise at room temperature. The mixture was heated at 45° C. for 2 hours. The obtained reaction mixture was added dropwise to 25% aqueous ammonia (325 ml) while keeping the mixture at 5-20° C. The mixture was stirred at room temperature for 1 hour. The crystals were filtered, washed with water and isopropyl ether and dried under reduced pressure to give 4-(trifluoromethyl)-cinnamamide (60.76 g, yield 94%). H-NMR (CDCl3-DMSO-d6, δ, 300 MHz) 5.93(1H,s), 6.53(1H,d,J=15.8 Hz), 6.75(1H,s), 7.48-7.53(5H,m).

Aufarbeitung

  1. customThe obtained reaction mixture
  2. customat 5-20° C
  3. filtrationThe crystals were filtered
  4. washwashed with water and isopropyl ether
  5. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2ff04043346a4b2baf5dcd990cc556ea
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743924B2

Notizen zur Reaktion

Wird geladen…