Trifluoroacetic anhydride → 5-Chloro-3-(methoxycarbonyl)-2-methylpyrazine 1-oxide

HRID 627690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627690
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([CH3:12])=[N:4][CH:3]=1.C(N)(N)=[O:14].OO.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([CH3:12])=[N+:4]([O-:14])[CH:3]=1

Komponenten

5

Edukt 3

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 57992035Methyl 6-chloro-3-methylpyrazine-2-carboxylate

Produkt 1

HCID 867281445-Chloro-3-(methoxycarbonyl)-2-methylpyrazine 1-oxideAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of methyl 6-chloro-3-methylpyrazine-2-carboxylate (8.6 g, 46.1 mmol) and hydrogen peroxide urea adduct (8.1 g, 86 mmol) in dichloromethane (100 mL) was added 2,2,2-trifluoroacetic anhydride (10.9 ml, 78 mmol) dropwise. The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with DCM and quenched with water. The aqueous layer was extracted with DCM. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to give the crude product 5-chloro-3-(methoxycarbonyl)-2-methylpyrazine 1-oxide (8.83 g, 43.6 mmol, 95% yield) which was used without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 8.31 (1H, s), 4.02 (3H, s), 2.65 (3H, s).

Aufarbeitung

  1. customquenched with water
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-744bd9f5361c4e71aefcf0cae120cc6f
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309263B2

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