Hydrogen Peroxide → 2,3-Dimethyl-1-oxo-1lambda~5~-pyrazine

HRID 507276Notes

Reaction equation

HRID 507276 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[N:6][CH:5]=[CH:4][N:3]=1.[OH:9]O>C(O)(=O)C>[CH3:1][C:2]1[C:7]([CH3:8])=[N:6][CH:5]=[CH:4][N+:3]=1[O-:9]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 222012,3-Dimethylpyrazine

Product 1

HCID 124071632,3-Dimethyl-1-oxo-1lambda~5~-pyrazineYield 94.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 2,3-dimethylpyrazine (25 g, 0.23 mol) and 30% H2O2 (52.4 g, 0.46 mol) in acetic acid (74 mL) was stirred for two days at 35° C. The solvent was removed under vacuum. Water was added and the mixture evaporated again. The residue was basified with aqueous K2CO3 and extracted with EtOAc. The organic phases were dried over Na2SO4 and concentrated. The resulting solid combined from two batches was recrystallized from cyclohexane to give 2,3-dimethylpyrazine 1-oxide (27 g, 47%). 1HNMR (CDCl3, 300 MHz) δ 8.18 (d, J=3.9 Hz, 1H), 8.02 (d, J=4.2 Hz, 1H), 2.58 (s, 3H), 2.48 (s, 3H).

Workup

  1. customThe solvent was removed under vacuum
  2. additionWater was added
  3. customthe mixture evaporated again
  4. extractionextracted with EtOAc
  5. dry with materialThe organic phases were dried over Na2SO4
  6. concentrationconcentrated
  7. customwas recrystallized from cyclohexane

Sources & evidence

ORD record
ord-bd24f7354f904409878097102f86b6ab
Source dataset
uspto-grants-2010_08
Patent number
US07786141B2

Reaction notes

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