5,6-dichloropyridine-3-carbonyl Chloride → 3-t-Butyl-5-(5,6-dichloro-3-pyridyl)-1,2,4-oxadiazole

HRID 368284Notes

Reaction equation

HRID 368284 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](Cl)=[O:10])[CH:5]=[N:6][C:7]=1[Cl:8].O[NH:13][C:14](=[NH:19])[C:15]([CH3:18])([CH3:17])[CH3:16]>C1(C)C=CC=CC=1>[C:15]([C:14]1[N:19]=[C:9]([C:4]2[CH:5]=[N:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[O:10][N:13]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 27821565,6-dichloropyridine-3-carbonyl ChlorideHCID 178446865HCID 178446865, compound

Product 1

HCID 232882723-t-Butyl-5-(5,6-dichloro-3-pyridyl)-1,2,4-oxadiazoleYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5,6-dichloro-pyridine-3-carbonyl chloride (1.8 g, 8.6 mmol) and N-hydroxy-2,2-dimethylpropanimidamide (1.0 g, 8.6 mmol) in toluene (40 mL) was stirred at room temperature for two hours and then heated under reflux for four hours. The mixture was cooled to room temperature and filtered through celite, the solids being washed with toluene (20 mL). Evaporation of the combined filtrates under reduced pressure gave the desired product (1.3 g, 56%) as a clear oil which crystallised on standing to a white solid, MP 98-101° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for four hours
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationfiltered through celite
  5. washthe solids being washed with toluene (20 mL)
  6. customEvaporation of the combined filtrates under reduced pressure

Sources & evidence

ORD record
ord-a91589b60f7c45e6ae0ca46b4c1d3979
Source dataset
uspto-grants-2000_10
Patent number
US06133294

Reaction notes

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