Pyridine → (E)-3-(3-chloro-2-fluoro-styryl)-5-trichloromethyl-1,2,4-oxadiazole

HRID 22366

Reaction equation

HRID 22366 reaction equation
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](Cl)=[O:4].[Cl:8][C:9]1[C:10]([F:21])=[C:11]([CH:18]=[CH:19][CH:20]=1)/[CH:12]=[CH:13]/[C:14](=[N:16]O)[NH2:15].N1C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:8][C:9]1[C:10]([F:21])=[C:11]([CH:18]=[CH:19][CH:20]=1)/[CH:12]=[CH:13]/[C:14]1[N:16]=[C:3]([C:2]([Cl:7])([Cl:6])[Cl:1])[O:4][N:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6420Trichloroacetyl chlorideHCID 86748305(E)-3-chloro-2-fluoro-cinnamamide oxime

Product 1

HCID 23364567(E)-3-(3-chloro-2-fluoro-styryl)-5-trichloromethyl-1,2,4-oxadiazoleYield 48.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

12.7 g (0.07 mol) of trichloroacetyl chloride are added dropwise to a suspension consisting of 6.4 g (0.03 mol) of (E)-3-chloro-2-fluoro-cinnamamide oxime in 90 ml of chloroform and 6 ml (0.07 mol) of dry pyridine. During this process, there is a slight evolution of heat. Subsequently, the mixture is stirred for 1 hour and the pyridine hydrochloride which separates out is filtered off and washed with chloroform. The filtrate is concentrated in vacuo and the remaining solid material is recrystallized. 5.0 g (48.7% of theory) of (E)-3-(3-chloro-2-fluoro-styryl)-5-trichloromethyl-1,2,4-oxadiazole are obtained.

Workup

  1. temperatureof heat
  2. filtrationthe pyridine hydrochloride which separates out is filtered off
  3. washwashed with chloroform
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe remaining solid material is recrystallized

Sources & evidence

ORD record
ord-ee72f4837e0f489eb3d751852d9ce809
Source dataset
uspto-grants-1995_06
Patent number
US05428049

Linked notes

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