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

HRID 22364Notes

Reaction equation

HRID 22364 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

HCID 23364564(E)-3-(3-chloro-2-fluoro-styryl)-5-methyl-1,2,4-oxadiazoleYield 75.6%

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-766b336206b54253b75934c0d224bd11
Source dataset
uspto-grants-1995_06
Patent number
US05428049

Reaction notes

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