Ethyl orthoformate → (E)-3-(4-chloro-3-trifluoromethyl-styryl)-1,2,4-oxadiazole

HRID 1081384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1081384
[Cl:1][C:2]1[CH:13]=[CH:12][C:5](/[CH:6]=[CH:7]/[C:8](=[N:10][OH:11])[NH2:9])=[CH:4][C:3]=1[C:14]([F:17])([F:16])[F:15].[CH:18](OCC)(OCC)OCC>B(F)(F)F.CCOCC>[Cl:1][C:2]1[CH:13]=[CH:12][C:5](/[CH:6]=[CH:7]/[C:8]2[N:9]=[CH:18][O:11][N:10]=2)=[CH:4][C:3]=1[C:14]([F:15])([F:16])[F:17]

Komponenten

4

Edukt 2

HCID 31214Ethyl orthoformateHCID 86748304(E)-4-chloro-3-trifluoromethyl-cinnamamide oxime

Produkt 1

HCID 23364566(E)-3-(4-chloro-3-trifluoromethyl-styryl)-1,2,4-oxadiazoleAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8000Boron trifluoride etherateKatalysator

Versuchsvorschrift

5.2 g (0.02 mol) of (E)-4-chloro-3-trifluoromethyl-cinnamamide oxime are introduced into 50 ml of triethyl orthoformate and 2 drops of boron trifluoride etherate are added at room temperature. The mixture is then stirred for 2 hours at reflux temperature and the entire batch is concentrated in vacuo. The residue is taken up in 100 ml of methylene chloride and washed in succession with 100 ml of 2N hydrochloric acid, saturated sodium carbonate solution and water. The organic phase is dried over sodium sulphate and the solvent is subsequently distilled off. 3.9 g (71.0 % of theory) of (E)-3-(4-chloro-3-trifluoromethyl-styryl)-1,2,4-oxadiazole are obtained.

Aufarbeitung

  1. additionare added at room temperature
  2. temperatureat reflux temperature
  3. concentrationthe entire batch is concentrated in vacuo
  4. washwashed in succession with 100 ml of 2N hydrochloric acid, saturated sodium carbonate solution and water
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. distillationthe solvent is subsequently distilled off

Quellen und Nachweise

ORD-Eintrag
ord-7789646b52324900b8f07f7469ef035e
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05585493

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