Potassium Carbonate → 5-Chloro-2-imino-1-[2-(methylsulfonyl)benzyl]-1,2-dihydropyridine-3-carboxamide hydrochloride

HRID 1015774ノート

反応式

HRID 1015774 の反応式
[C:1]([CH:3]([CH:7]1[C:11]([Cl:12])=[C:10](Cl)C(=O)O1)[C:4]([NH2:6])=[O:5])#[N:2].Cl.[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][NH2:27])(=[O:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>C(O)C>[ClH:12].[Cl:12][C:11]1[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:1](=[NH:2])[N:27]([CH2:26][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[S:17]([CH3:16])(=[O:19])=[O:18])[CH:10]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 162183342-(Methanesulfonyl)benzylamine hydrochloride

生成物 1

HCID 669701345-Chloro-2-imino-1-[2-(methylsulfonyl)benzyl]-1,2-dihydropyridine-3-carboxamide hydrochloride収率 20.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2-Cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (1.8 g), 1-[2-(methylsulfonyl)phenyl]methanamine hydrochloride (1.5 g) and potassium carbonate (1.8 g) were stirred in ethanol (30 ml) at 80° C. for 16 hr. The reaction mixture was poured into 1N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate). The obtained residue was dissolved in methanol, 4N hydrogen chloride-ethyl acetate solution (2 ml) was added, and the mixture was crystallized from methanol-ethyl acetate. The precipitated crystals were collected by filtration, and recrystallized to give the title compound (0.29 g).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (ethyl acetate)
  7. dissolutionThe obtained residue was dissolved in methanol
  8. addition4N hydrogen chloride-ethyl acetate solution (2 ml) was added
  9. customthe mixture was crystallized from methanol-ethyl acetate
  10. filtrationThe precipitated crystals were collected by filtration
  11. customrecrystallized

出典と根拠

ORDレコード
ord-eae1b5d53c7b4edfb8a04b492a7887f1
出典データセット
uspto-grants-2011_07
特許番号
US07985862B2

反応ノート

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