Acetyl nitrate → 5-Nitrouracil

HRID 1817790

Reaction equation

HRID 1817790 reaction equation
[N:1]([O-:3])=[O:2].[Na+].[CH3:5][C:6]([OH:8])=O.[N+]([O-])(O)=O.OS(O)(=O)=O.N(O)=O.C(O[N+]([O-])=O)C.CC(O[N+]([O-])=O)=O.N([N:36]1[C:41](=O)C=C[NH:38][C:37]1=[O:43])=O.N[N:45]1[C:50](=O)C=C[NH:47][C:46]1=[O:52].N([O-])=O.[Na+]>C(O)(=O)C.O>[N+:1]([C:5]1[C:6](=[O:8])[NH:38][C:37](=[O:43])[NH:36][CH:41]=1)([O-:3])=[O:2].[N:1]([C:5]1[C:6](=[O:8])[NH:47][C:46](=[O:52])[NH:45][CH:50]=1)=[O:3]

Participants

12

Reactant 8

HCID 11557Acetyl nitrateHCID 12259Ethyl NitrateHCID 24529Nitrous AcidHCID 1487822,4(1H,3H)-Pyrimidinedione, amino-2×HCID 23668193Sodium NitriteHCID 71777668Sulfuric acid, mixt. with nitric acidHCID 86611488NaNO2 acetic acidHCID 866114893-nitroso-1H-pyrimidine-2,4-dione

Product 2

HCID 691355-NitrouracilHCID 3283635-Nitrosouracil

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

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, HNO3/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.

Workup

  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

Sources & evidence

ORD record
ord-233bf0d5a0a94d0699bfbbc82bef1539
Source dataset
uspto-grants-2009_10
Patent number
US07598379B2

Linked notes

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