Acetic Acid → 2-[(2,5-Dimethylphenyl)methanesulfonyl]-4-methyl-1-oxo-1lambda~5~-pyridine

HRID 1829737Notes

Reaction equation

HRID 1829737 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N+:12]=1[O-:18].OO.[OH2:21].C(O)(=[O:24])C>[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][S:10]([C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N+:12]=1[O-:18])(=[O:24])=[O:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 131787432-{[(2,5-Dimethylphenyl)methyl]sulfanyl}-4-methyl-1-oxo-1lambda~5~-pyridine

Product 1

HCID 131787442-[(2,5-Dimethylphenyl)methanesulfonyl]-4-methyl-1-oxo-1lambda~5~-pyridine

Reagents, catalysts & solvents 1

HCID 26052Sodium tungstateCatalyst

Conditions

Temperature
40 °C

Procedure

The sulfide isolated in step (a) above was dissolved in 20 ml of glacial acetic acid and 1.5 ml of 30% hydrogen peroxide was added along with 100 mg of sodium tungstate. The reaction mixture was heated at 40° C. for one hour, cooled, and poured into water to percipitate the product. Yield, 1.46 or 89%. NMR supported the proposed structure.

Workup

  1. temperaturecooled
  2. customYield

Sources & evidence

ORD record
ord-931cc647bf224d12a8bd2c23f5789b52
Source dataset
uspto-grants-2006_06
Patent number
US07064139B2

Reaction notes

Loading…