Pivaloyl chloride → 5-(t-Butyl)-3-(5,6-dichloro-3-pyridinyl)-1,2,4-oxadiazole

HRID 368281Notes

Reaction equation

HRID 368281 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[NH:12])[NH:10][OH:11])[CH:5]=[N:6][C:7]=1[Cl:8].[CH3:13][C:14]([CH3:19])([CH3:18])[C:15](Cl)=O>C1(C)C=CC=CC=1>[C:14]([C:19]1[O:11][N:10]=[C:9]([C:4]2[CH:5]=[N:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[N:12]=1)([CH3:18])([CH3:15])[CH3:13]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 178513387HCID 178513387, compound

Product 1

HCID 232882825-(t-Butyl)-3-(5,6-dichloro-3-pyridinyl)-1,2,4-oxadiazoleYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5,6-Dichloro-N-hydroxy-3-pyridinecarboximidamide (3.0 g, 0.015 mol) was slurried in toluene (30 mL) and trimethylacetyl chloride (1.93 g, 0.016 mol) added. The mixture was stirred at room temperature for one hour and then heated under reflux conditions for four hours. This was then cooled and filtered through Celite, washing with additional toluene (20 mL). Evaporation of the solvent under reduced pressure and purification of the residue by chromatography over silica (0-10% ethyl acetate:hexane) gave the desired product as a white solid (2.77 g, 68%).

Workup

  1. temperatureheated under reflux conditions for four hours
  2. temperatureThis was then cooled
  3. filtrationfiltered through Celite
  4. washwashing with additional toluene (20 mL)
  5. customEvaporation of the solvent
  6. customunder reduced pressure and purification of the residue by chromatography over silica (0-10% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-c0773ffbf30d4005851044f0297e85dc
Source dataset
uspto-grants-2000_10
Patent number
US06133294

Reaction notes

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