Acetyl nitrate → 5-Nitrouracil

HRID 1888925

Reaktionsgleichung

Reaktionsgleichung von HRID 1888925
[N:1]([O-:3])=[O:2].[Na+].CC(O)=O.N(O)=O.C(O[N+]([O-])=O)C.CC(O[N+]([O-])=O)=O.N([N:27]1[C:32](=[O:33])[CH:31]=[CH:30][NH:29][C:28]1=[O:34])=O.N[N:36]1[C:41](=[O:42])[CH:40]=[CH:39][NH:38][C:37]1=[O:43].N([O-])=O.[Na+]>C(O)(=O)C.O>[N+:1]([C:31]1[C:32](=[O:33])[NH:27][C:28](=[O:34])[NH:29][CH:30]=1)([O-:3])=[O:2].[N:1]([C:40]1[C:41](=[O:42])[NH:36][C:37](=[O:43])[NH:38][CH:39]=1)=[O:3]

Komponenten

11

Edukt 7

HCID 11557Acetyl nitrateHCID 12259Ethyl NitrateHCID 24529Nitrous AcidHCID 1487822,4(1H,3H)-Pyrimidinedione, amino-2×HCID 23668193Sodium NitriteHCID 86611488NaNO2 acetic acidHCID 866114893-nitroso-1H-pyrimidine-2,4-dione

Produkt 2

HCID 691355-NitrouracilHCID 3283635-Nitrosouracil

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

The 5-nitrosouracil derivatives such as compound of the formula 4 may be obtained by the nitrosylation of the aminouracil 2 using standard nitration reagents. Examples of such agents include, for example, NaNO2/AcOH, 1-INO3/H2SO4, N2O5/P2O5/CCl4, HONO, EtONO2, CH3COONO2 and NO2+CF3SO3− that forms the nitro or the nitrosouracil derivative. Thus, the aminouracil 2 may be dissolved in an aqueous acid, such as acetic acid and water below room temperature, such as about 10° C., and NaNO2 in water is added to the aminouracil. When the reaction is deemed complete, the volatiles are removed under reduced pressure and the residue is redissolved in a mixture of solvents. Example of such mixtures of solvents include alcohols in an organic solvent, such as absolute ethanol in DICHLOROMETHANE. The resulting mixture is heated and the hot mixture may be filtered through a filter aid such as Celite 545 to remove insoluble inorganic salts. The solvent or solvent mixtures may evaporated under reduced pressure to afford the desired 5-nitrouracil or 5-nitrosouracil such as compound 4.

Aufarbeitung

  1. customthe volatiles are removed under reduced pressure
  2. dissolutionthe residue is redissolved in a mixture of solvents
  3. temperatureThe resulting mixture is heated
  4. filtrationthe hot mixture may be filtered through a filter aid such as Celite 545
  5. customto remove insoluble inorganic salts
  6. customThe solvent or solvent mixtures may evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-33aee6f70ccb4c3a9bc3543d284c2651
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501941B2

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