Potassium Carbonate → HCID 66969583, compound

HRID 1015887Notes

Reaction equation

HRID 1015887 reaction equation
[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.[NH2:16][CH2:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[NH:25][C:26](=[O:29])[O:27]C.[C:30](=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>C(O)C>[ClH:12].[CH3:30][N:25]([C:19]1[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=1[CH2:17][N:16]1[CH:10]=[C:11]([Cl:12])[CH:7]=[C:3]([C:4](=[O:5])[NH2:6])[C:1]1=[NH:2])[C:26](=[O:29])[OH:27]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 66878502HCID 66878502, compound

Product 1

HCID 66969583HCID 66969583, compoundYield 4.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(Step 4) 2-Cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (1.0 g), methyl [2-(aminomethyl)-4-chlorophenyl]carbamate hydrochloride obtained in Step 3 (2.12 g) and potassium carbonate (1.18 g) were stirred in ethanol (10 ml) overnight at 80° C. 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:hexane=7:3→1:0). The obtained residue was dissolved in ethanol, 4N hydrogen chloride-ethyl acetate solution (2 ml) was added, and the mixture was crystallized from ethanol-ethyl acetate. The precipitated crystals were collected by filtration, and recrystallized to give the title compound (42 mg).

Workup

  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:hexane=7:3→1:0)
  7. dissolutionThe obtained residue was dissolved in ethanol
  8. addition4N hydrogen chloride-ethyl acetate solution (2 ml) was added
  9. customthe mixture was crystallized from ethanol-ethyl acetate
  10. filtrationThe precipitated crystals were collected by filtration
  11. customrecrystallized

Sources & evidence

ORD record
ord-2f043ddcc25d437ab23e7ed39d83ab86
Source dataset
uspto-grants-2011_07
Patent number
US07985863B2

Reaction notes

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