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

HRID 1074844Notes

Reaction equation

HRID 1074844 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:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N+:13]=1[O-:19])=[O:11].[OH-:20].[Na+].[CH3:22]I>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH:9]([S:10]([C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N+:13]=1[O-:19])(=[O:20])=[O:11])[CH3:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 501194Pyridine, 2-[[(2,5-dimethylphenyl)methyl]sulfinyl]-3-methyl-, 1-oxide

Product 1

HCID 501193Pyridine, 2-[[1-(2,5-dimethylphenyl)ethyl]sulfonyl]-3-methyl-, 1-oxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 3 g (0.01 mol) of sulfone (described in Example 3) in 15 mL of dry dimethylformamide cooled in an ice bath, is added 0.5 g sodium hydroxide powder. To this mixture is slowly added 0.75 mL methyl iodide. The reaction mixture is warmed to room temperature and stirred for 2 hours. 100 mL ice-water is slowly added with stirring. After filtration the white solid is recrystallized from toluene. Melting point: 146°-147° C. Structure confirmed by NMR. I.R. N→O 1250 cm-1, SO2 1350, 1140 cm-1.

Workup

  1. temperaturecooled in an ice bath
  2. stirringwith stirring
  3. filtrationAfter filtration the white solid
  4. customis recrystallized from toluene

Sources & evidence

ORD record
ord-3f446f9dcafd45a79de8a5091ae75ef7
Source dataset
uspto-grants-1983_07
Patent number
US04394155

Reaction notes

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