Dimethyl Sulfate → 3,5-Dimethyl-4-nitropyridine-N-Oxide dimethyl Sulphate

HRID 1067032Notes

Reaction equation

HRID 1067032 reaction equation
[CH3:1][C:2]1[CH:3]=[N+:4]([O-:12])[CH:5]=[C:6]([CH3:11])[C:7]=1[N+:8]([O-:10])=[O:9].[S:13]([O:18][CH3:19])([O:16][CH3:17])(=[O:15])=[O:14]>CC(C)=O>[CH3:1][C:2]1[CH:3]=[N+:4]([O-:12])[CH:5]=[C:6]([CH3:11])[C:7]=1[N+:8]([O-:10])=[O:9].[S:13]([O:18][CH3:19])([O:16][CH3:17])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 96264Pyridine, 3,5-dimethyl-4-nitro-, 1-oxide

Product 1

HCID 867570023,5-Dimethyl-4-nitropyridine-N-Oxide dimethyl SulphateYield 93.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 3,5-Dimethyl-4-nitropyridine-N-Oxide (V) (150 gm, 0.80 mole) in acetone (450 ml) was added dimethyl sulfate (90 ml, 0.95 mole). The mixture was heated to reflux until a clear solution was obtained and then allowed to cool to ambient temperature. An off-white crystalline solid separated out, which was filtered, washed with acetone and dried to yield 220 gm of the adduct. Yield was 83.8% of theoretical.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux until a clear solution
  3. customwas obtained
  4. customAn off-white crystalline solid separated out
  5. filtrationwhich was filtered
  6. washwashed with acetone
  7. customdried

Sources & evidence

ORD record
ord-13b0bf7486f54370bc2f75bf12dfb511
Source dataset
uspto-grants-2001_06
Patent number
US06245913B1

Reaction notes

Loading…