Methyl iodide → 5-Nitro-1-methyl-uracil

HRID 2257116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2257116
[N+:1]([C:4]1[C:5](=[O:11])[NH:6][C:7](=[O:10])[NH:8][CH:9]=1)([O-:3])=[O:2].[C:12](=O)([O-])[O-].[K+].[K+].IC.[OH-].[Na+]>CN(C)C=O.O>[N+:1]([C:4]1[C:5](=[O:11])[NH:6][C:7](=[O:10])[N:8]([CH3:12])[CH:9]=1)([O-:3])=[O:2]

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 691355-Nitrouracil

Produkt 1

HCID 27557345-Nitro-1-methyl-uracilAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-nitrouracil (10.00 g, 64 mmole) and potassium carbonate were stirred in dimethylformamide (50 mL) for 15 min. A solid formed. Iodomethane (5.3 mL, 85 mmol) was added and the flask was shaken until the solid dissolved. After the reaction mixture was stirred for 30 min., 2% NaOH (w/v) (200 mL) was added, followed by water (100 mL). The solution was washed with ethyl acetate (100 mL), and the aqueous layer was acidified to pH 3 with 1.0N HCl. A precipitate formed as the pH was lowered. After allowing the heterogeneous solution to stand for 16 hours, the product was filtered, washing with water, and air dried. The title compound was isolated in 77% yield as a yellow powder. m.p. 249°-250° C.

Aufarbeitung

  1. customA solid formed
  2. dissolutiondissolved
  3. stirringAfter the reaction mixture was stirred for 30 min.
  4. washThe solution was washed with ethyl acetate (100 mL)
  5. customA precipitate formed as the pH
  6. filtrationthe product was filtered
  7. washwashing with water, and air
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-26fb828977dd4cdc86b76f0be61741c6
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05656645

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