Acetyl nitrate → 5-Nitrouracil

HRID 1818728

反応式

HRID 1818728 の反応式
[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]

参加物

12

反応物 8

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

生成物 2

HCID 691355-NitrouracilHCID 3283635-Nitrosouracil

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒2 回

実験手順

The 5-nitrosouracil derivative may be obtained by the nitrosylation of the aminouracil A 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 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.

後処理

  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

出典と根拠

ORDレコード
ord-7513a4927c1b44d7b9a1a320126d79b9
出典データセット
uspto-grants-2009_10
特許番号
US07601723B2

関連ノート

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