Pyridine → (E)-3-(3-chloro-2-fluoro-styryl)-5-trichloromethyl-1,2,4-oxadiazole

HRID 22366

Reaktionsgleichung

Reaktionsgleichung von HRID 22366
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](Cl)=[O:4].[Cl:8][C:9]1[C:10]([F:21])=[C:11]([CH:18]=[CH:19][CH:20]=1)/[CH:12]=[CH:13]/[C:14](=[N:16]O)[NH2:15].N1C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:8][C:9]1[C:10]([F:21])=[C:11]([CH:18]=[CH:19][CH:20]=1)/[CH:12]=[CH:13]/[C:14]1[N:16]=[C:3]([C:2]([Cl:7])([Cl:6])[Cl:1])[O:4][N:15]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6420Trichloroacetyl chlorideHCID 86748305(E)-3-chloro-2-fluoro-cinnamamide oxime

Produkt 1

HCID 23364567(E)-3-(3-chloro-2-fluoro-styryl)-5-trichloromethyl-1,2,4-oxadiazoleAusbeute 48,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

12.7 g (0.07 mol) of trichloroacetyl chloride are added dropwise to a suspension consisting of 6.4 g (0.03 mol) of (E)-3-chloro-2-fluoro-cinnamamide oxime in 90 ml of chloroform and 6 ml (0.07 mol) of dry pyridine. During this process, there is a slight evolution of heat. Subsequently, the mixture is stirred for 1 hour and the pyridine hydrochloride which separates out is filtered off and washed with chloroform. The filtrate is concentrated in vacuo and the remaining solid material is recrystallized. 5.0 g (48.7% of theory) of (E)-3-(3-chloro-2-fluoro-styryl)-5-trichloromethyl-1,2,4-oxadiazole are obtained.

Aufarbeitung

  1. temperatureof heat
  2. filtrationthe pyridine hydrochloride which separates out is filtered off
  3. washwashed with chloroform
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe remaining solid material is recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-ee72f4837e0f489eb3d751852d9ce809
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428049

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