Acetyl nitrate → 5-Nitrouracil

HRID 2105170

반응식

HRID 2105170 반응식
[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]

참가 물질

11

반응물 7

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

생성물 2

HCID 691355-NitrouracilHCID 3283635-Nitrosouracil

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매2회

실험 절차

The 5-nitrosouracil derivative may be obtained by the nitrosylation of the aminouracil A or B using standard nitration reagents. Examples of such agents include, for example, NaNO2/AcOH, NHO3/H2SO4, N2O5/P2O5/CCl4, HONO, EtONO2, CH3COONO2 and NO2+CF3SO3− that forms the nitro or the nitrosouracil derivative. Thus, the aminouracil 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 DCM. 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.

후처리

  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

출처 및 근거

ORD 기록
ord-f0e0ecdf1848467e9d71cee5da763dac
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579348B2

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