m-Chloroperbenzoic acid → 3-(2,4-Dichlorophenyl)-2,5-dimethylpyrazine 1-oxide

HRID 1824063Notes

Reaction equation

HRID 1824063 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([CH3:16])=[N:11][CH:12]=[C:13]([CH3:15])[N:14]=1.C1C=C(Cl)C=C(C(OO)=[O:25])C=1>O1CCOCC1.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([CH3:16])=[N+:11]([O-:25])[CH:12]=[C:13]([CH3:15])[N:14]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 221473513-(2,4-Dichlorophenyl)-2,5-dimethylpyrazine

Product 1

HCID 221472913-(2,4-Dichlorophenyl)-2,5-dimethylpyrazine 1-oxide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 3-(2,4-dichlorophenyl)-2,5-dimethylpyrazine at 0° C. in dioxane was added mCPBA (750 mg). The reaction mixture was heated at 45° C. for 3 h. The reaction was diluted with CH2Cl2, washed with NaHCO3 dried (MgSO4), filtered, and concentrated. It was used without purification: 1H NMR (CDCl3) δ 2.30, 2.54, 7.33, 7.42, 7.54, 8.13; 13C NMR (CDCl3) δ 14.04, 21.85, 128.10, 130.12, 131.64, 132.14, 134.07, 135.23, 136.44, 141.66, 153.87, 154.24.

Workup

  1. washwashed with NaHCO3
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customIt was used without purification

Sources & evidence

ORD record
ord-4ab9d196ff9b41959689216e688c6f58
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

Loading…