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Butyl bromide → 4-butyl-2H-[1,2,4]triazine-3,5-dione

HRID 232558
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 232558
[H-].[Na+].C([N:6]1[C:11](=[O:12])[NH:10][C:9](=[O:13])[CH:8]=[N:7]1)(=O)C.Br[CH2:15][CH2:16][CH2:17][CH3:18]>CN(C=O)C>[CH2:15]([N:10]1[C:9](=[O:13])[CH:8]=[N:7][NH:6][C:11]1=[O:12])[CH2:16][CH2:17][CH3:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 212565952-Acetyl-1,2,4-triazine-3,5(2H,4H)-dione

Produkt 1

HCID 152295424-butyl-2H-[1,2,4]triazine-3,5-dioneAusbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a 50% sodium hydride suspension (4.8 g) in DMF (100 ml), compound 11a (15.5 g) dissolved in DMF (200 ml) is added drop by drop, maintaining the temperature at room temperature. After agitation for 2 hours, bromobutane (20 g) is added and the agitation continued for 12 hours. The reaction mixture is concentrated to dryness under vacuum at 60° C., taken up in water, and then extracted with methylene chloride. After concentration to dryness under vacuum, the oil is taken up in ethanol (100 ml), whereupon p-toluene-sulfonic acid (2 g) is added. After heating under reflux for 2 hours and leaving at room temperature for 12 hours, the reaction mixture is filtered. The precipitate is washed with an aqueous solution of sodium bicarbonate and water, and then dried in an oven under vacuum in order to give the compound 11b (8.7 g).

Aufarbeitung

  1. additionis added drop by drop
  2. waitthe agitation continued for 12 hours
  3. concentrationThe reaction mixture is concentrated to dryness under vacuum at 60° C.
  4. extractionextracted with methylene chloride
  5. concentrationAfter concentration to dryness under vacuum
  6. additionwhereupon p-toluene-sulfonic acid (2 g) is added
  7. temperatureAfter heating
  8. temperatureunder reflux for 2 hours
  9. customleaving at room temperature for 12 hours
  10. filtrationthe reaction mixture is filtered
  11. washThe precipitate is washed with an aqueous solution of sodium bicarbonate and water
  12. customdried in an oven under vacuum in order

Quellen und Nachweise

ORD-Eintrag
ord-6974236b42d44bc78784a6372609c773
Quelldatensatz
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05591743

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