Hydrogen Peroxide → 5-(4-Formylphenoxy)pyrazine-2-carboxamide

HRID 130874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 130874
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[N:9]=[CH:10][C:11]([C:14]#[N:15])=[N:12][CH:13]=2)=[CH:5][CH:4]=1)=[O:2].C([O-])([O-])=[O:19].[K+].[K+].OO>CS(C)=O.C(Cl)Cl>[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[N:9]=[CH:10][C:11]([C:14]([NH2:15])=[O:19])=[N:12][CH:13]=2)=[CH:5][CH:4]=1)=[O:2]

Komponenten

6

Edukt 3

HCID 784Hydrogen PeroxideHCID 11430Potassium Carbonate2×HCID 597301105-(4-Formylphenoxy)pyrazine-2-carbonitrile

Produkt 1

HCID 597301885-(4-Formylphenoxy)pyrazine-2-carboxamideAusbeute 47,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Dissolve 5-(4-formylphenoxy)pyrazine-2-carbonitrile (1.87 g, 8.30 mmol) and K2CO3 (0.573 g, 4.15 mmol) in DMSO (21 mL). Add 30% H2O2 (2.4 mL, 20.8 mmol) and stir at room temperature for 22 hours. Add additional K2CO3 (0.573 g, 4.15 mmol) and heat at 55° C for about 2.5 hours. Cool the reaction mixture and dilute with CH2Cl2, (200 mL). Wash with water (1×100 (mL) and saturated aqueous NaHCO3 (1×100 mL). Dry the organic layer over Na2SO4, filter and concentrate. Purify by flash chromatography, eluting with 0-50% ethyl acetate in dichloromethane to give the title compound (0.478 g, 23.7%): TOF MS ES+ 244.1 (M+H)+, HRMS calcd for C12H10N33 244.0722 (M+H)+, found 244.0709, time 0.38 min; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 20-99% over 23 min], tR=7.2 min, 100% purity.

Aufarbeitung

  1. temperatureheat at 55° C for about 2.5 hours
  2. temperatureCool the reaction mixture
  3. washWash with water (1×100 (mL) and saturated aqueous NaHCO3 (1×100 mL)
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by flash chromatography
  8. washeluting with 0-50% ethyl acetate in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-71d56e23614c444385fc93c1cb1c97cb
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381719B2

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