Hydrochloric Acid → 4-(Phenylcarbonyl)-1,2,4-triazine-3,5(2H,4H)-dione

HRID 1513339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1513339
C([N:4]1[C:9](=[O:10])[NH:8][C:7](=[O:11])[CH:6]=[N:5]1)(=O)C.N1C=CC=CC=1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>O1CCOCC1>[C:19]1([C:18]([N:8]2[C:7](=[O:11])[CH:6]=[N:5][NH:4][C:9]2=[O:10])=[O:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7412Benzoyl chloride2×HCID 212565952-Acetyl-1,2,4-triazine-3,5(2H,4H)-dione

Produkt 1

HCID 128501114-(Phenylcarbonyl)-1,2,4-triazine-3,5(2H,4H)-dioneAusbeute 23,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 2-acetyl-1,2,4-triazine-3,5(2H,4H)-dione (1.05 g, 6.77 mmol) in 1,4-dioxane (11 ml) and pyridine (1.64 ml, 20.31 mmol) was treated dropwise at 5° C. with benzoyl chloride (0.90 ml, 7.78 mmol), then the mixture was stirred at room temperature overnight. The day after, 0.1 eq of benzoyl chloride was added and the mixture was stirred at rt for further 4 hours. The reaction mixture was then filtered to remove the piridinium salt and the filtered was evaporated under vacuum. The residue was dissolved in ethanol (23 ml) and then hydrochloride acid 37% (0.74 ml, 24.19 mmol) was added and the reaction was refluxed for 15 minutes. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica eluting with a gradient of methanol in DCM (from 0 to 4%) to afford the title compound as a white solid (0.35 g, 23.47%).

Aufarbeitung

  1. stirringthe mixture was stirred at rt for further 4 hours
  2. filtrationThe reaction mixture was then filtered
  3. customto remove the piridinium salt
  4. customthe filtered was evaporated under vacuum
  5. dissolutionThe residue was dissolved in ethanol (23 ml)
  6. temperaturethe reaction was refluxed for 15 minutes
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by column chromatography on silica eluting with a gradient of methanol in DCM (from 0 to 4%)

Quellen und Nachweise

ORD-Eintrag
ord-eb68c2debea54dcf90ed4ea2b939aa75
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217168B2

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