Pivaloyl chloride → HCID 23288280, compound

HRID 368283Notes

Reaction equation

HRID 368283 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10](=[NH:13])[NH:11][OH:12])[CH:5]=[N:6][C:7]=1[S:8][CH3:9].[CH3:14][C:15]([CH3:20])([CH3:19])[C:16](Cl)=O>C1(C)C=CC=CC=1>[C:15]([C:20]1[O:12][N:11]=[C:10]([C:4]2[CH:5]=[N:6][C:7]([S:8][CH3:9])=[C:2]([Cl:1])[CH:3]=2)[N:13]=1)([CH3:19])([CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 178503455HCID 178503455, compound

Product 1

HCID 23288280HCID 23288280, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Chloro-6-methylthio-N-hydroxy-3-pyridinecarboximidamide (1.0 g, 4.6 mmol) was slurried in toluene (20 mL) and trimethylacetyl chloride (0.61 g, 5.1 mmol) 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 (0.77 g, 59%).

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-c66f7167ac46466a8d6898203d3901d1
Source dataset
uspto-grants-2000_10
Patent number
US06133294

Reaction notes

Loading…