Sodium Thiosulfate → 2-phenyl-6-methyl-pyridine-N-oxide

HRID 2288623Notes

Reaction equation

HRID 2288623 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:22])C=1.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N+:8]=2[O-:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 27628852-Methyl-6-phenylpyridine

Product 1

HCID 6036032-phenyl-6-methyl-pyridine-N-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

While stirring at room temperature, 4.8 g (28.5 mmol) of 2-phenyl-6-methyl-pyridine were dissolved in 50 ml of chloroform after which a solution of 7.8 g of 75% mCPBA (33.9 mmol) in 75 ml of chloroform were added dropwise. The reaction mixture showed only a slight rise in temperature. After stirring for 1.5 hr, the reaction mixture was shaken twice with 5% aqueous NaHCO3 solution and twice with an aqueous solution of Na2S2O3 to remove the excess of mCPBA, after which the reaction mixture proved to be negative on wet Kl/starch paper, The organic layer was dried on MgSO4. Removal of the drying agent by filtration and solvent by evaporation in vacuo yielded an oil which crystallized upon scratching to give 5.5 g (105%) of crude of 2-phenyl-6-methyl-pyridine-N-oxide, which was employed in the next step without further purification.

Workup

  1. additionwere added dropwise
  2. stirringAfter stirring for 1.5 hr
  3. customto remove the excess of mCPBA
  4. customThe organic layer was dried on MgSO4
  5. customRemoval of the drying agent
  6. filtrationby filtration and solvent
  7. customby evaporation in vacuo
  8. customyielded an oil which
  9. customcrystallized

Sources & evidence

ORD record
ord-528327bf7deb4bc3a742ef119fc17deb
Source dataset
uspto-grants-2000_07
Patent number
US06090812

Reaction notes

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