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

HRID 1081385Notes

Reaction equation

HRID 1081385 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 introduced into 50 ml of acetic anhydride and the mixture is stirred for 2 hours at reflux temperature. The entire batch is subsequently concentrated in vacuo, the residue is stirred with sodiumcarbonate solution and the mixture is 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-1,2,4-oxadiazole are obtained.

Workup

  1. temperatureat reflux temperature
  2. concentrationThe entire batch is subsequently concentrated in vacuo
  3. stirringthe residue is stirred with sodiumcarbonate solution
  4. extractionthe mixture is extracted 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-5c308677b71845898a88a7a1186b545a
Source dataset
uspto-grants-1996_12
Patent number
US05585493

Reaction notes

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