Water → Pyridine, 2-[[(2,5-dimethylphenyl)methyl]sulfonyl]-3-methyl-, 1-oxide

HRID 1829735Notes

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[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][N+:12]=1[O-:18].[OH:19]OS([O-])=O.[K+].[OH2:25]>CO>[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[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][N+:12]=1[O-:18])(=[O:19])=[O:25]

Participants

Conditions

Temperature: 24 °C

Procedure

To a stirred solution of 4.0 g of 2-[((2,5-dimethylphenyl)methyl)thio]-3-methylpyridine-1-oxide in 50 mL of methanol, cooled to 3° C., was added a solution of 14.1 g of Oxone® in 50 mL of water over a period of 50 minutes. The reaction mixture was stirred at 24° C. overnight and then diluted with 200 mL of water. The product was extracted into chloroform and dried over magnesium sulfate. Evaporation of solvent under reduced pressure gave 4.1 g of 2-[((2,5-dimethylphenyl)methyl)sulfonyl]-3-methylpyridine-1-oxide as a white crystalline solid, having a melting point of 171–173° C. The 1H NMR spectrum (CDCl3) was in agreement with the expected structure.

Workup

extractionThe product was extracted into chloroform
dry with materialdried over magnesium sulfate
customEvaporation of solvent under reduced pressure

Sources & evidence

ORD record: ord-d95b33a64a194054a549499545d5d6ea
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064139B2

Reaction notes

Loading…