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

HRID 1491970Notes

Reaction equation

HRID 1491970 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.Cl.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

6

Reactant 4

HCID 1049PyridineHCID 6420Trichloroacetyl chlorideHCID 10176127Pyridinium 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 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 the temperature of the reaction mixture rises slightly. Stirring is subsequently continued for 1 hour, and the pyridine hydrochloride which separates out in this process is filtered off and washed with chloroform. The filtrate is concentrated in vacuo and the solid which remains is recrystallised. 5.0 g (48.7% of theory) of (E)-3-(3-chloro-2-fluoro-styryl)-5-tri-chloromethyl-1,2,4-oxadiazole are obtained.

Workup

  1. filtrationis filtered off
  2. washwashed with chloroform
  3. concentrationThe filtrate is concentrated in vacuo
  4. customthe solid which remains is recrystallised

Sources & evidence

ORD record
ord-2de32a29ef4640d3ba4400cd2becfd42
Source dataset
uspto-grants-1994_12
Patent number
US05371231

Reaction notes

Loading…