Acetic Anhydride → (E)-3-(3-chloro-2-fluoro-styryl)-5-methyl-1,2,4-oxadiazole

HRID 22364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 22364
[Cl:1][C:2]1[C:3]([F:14])=[C:4]([CH:11]=[CH:12][CH:13]=1)/[CH:5]=[CH:6]/[C:7](=[N:9][OH:10])[NH2:8].[C:15](OC(=O)C)(=O)[CH3:16]>>[Cl:1][C:2]1[C:3]([F:14])=[C:4]([CH:11]=[CH:12][CH:13]=1)/[CH:5]=[CH:6]/[C:7]1[N:8]=[C:15]([CH3:16])[O:10][N:9]=1

Komponenten

3

Edukt 2

HCID 7918Acetic AnhydrideHCID 86748305(E)-3-chloro-2-fluoro-cinnamamide oxime

Produkt 1

HCID 23364564(E)-3-(3-chloro-2-fluoro-styryl)-5-methyl-1,2,4-oxadiazoleAusbeute 75,6 %

Versuchsvorschrift

6.4 g (0.03 mol) of (E)-3-chloro-2-fluoro-cinnamamide oxime are initially introduced into 50 ml of acetic anhydride and the mixture is then stirred at reflux temperature for 2 hours. Subsequently, the whole batch is concentrated in vacuo and the residue is stirred with sodium carbonate solution and extracted with methylene chloride. The organic phase is dried over sodium sulphate and the solvent is distilled off. 5.1 g (75.6% of theory) of (E)-3-(3-chloro-2-fluoro-styryl)-5-methyl-l,2,4-oxadiazole are obtained.

Aufarbeitung

  1. temperatureat reflux temperature for 2 hours
  2. concentrationSubsequently, the whole batch is concentrated in vacuo
  3. stirringthe residue is stirred with sodium carbonate solution
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. distillationthe solvent is distilled off

Quellen und Nachweise

ORD-Eintrag
ord-766b336206b54253b75934c0d224bd11
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428049

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