Propionic anhydride → (E)-3-(2,3-dichloro-styryl)-5-ethyl-1,2,4-oxadiazole

HRID 22365

Reaction equation

HRID 22365 reaction equation
[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:3]=1/[CH:4]=[CH:5]/[C:6](=[N:8][OH:9])[NH2:7].[C:15](OC(=O)CC)(=O)[CH2:16][CH3:17]>>[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:3]=1/[CH:4]=[CH:5]/[C:6]1[N:7]=[C:15]([CH2:16][CH3:17])[O:9][N:8]=1

Participants

3

Reactant 2

HCID 31263Propionic anhydrideHCID 86748752(E)-2,3-dichlorocinnamamide oxime

Product 1

HCID 21751478(E)-3-(2,3-dichloro-styryl)-5-ethyl-1,2,4-oxadiazoleYield 58.2%

Procedure

7.0 g (0.03 tool) of (E)-2,3-dichlorocinnamamide oxime are initially introduced into 7 ml of propionic 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. 4.7 g (58.2% of theory) of (E) -3- (2,3 -dichloro-styryl) -5-ethyl-1,2,4-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-a5c6763878c1464587c4cf8a8d4436e0
Source dataset
uspto-grants-1995_06
Patent number
US05428049

Linked notes

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