Potassium Carbonate → HCID 66970133, compound

HRID 1013985Notes

Reaction equation

HRID 1013985 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.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][NH2:24])=[C:19]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:18]=1.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:24]([CH2:23][C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][C:19]=2[S:25]([CH3:28])(=[O:27])=[O:26])[CH:10]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 16753947HCID 16753947, compound

Product 1

HCID 66970133HCID 66970133, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (3.0 g), 1-[4-fluoro-2-(methylsulfonyl)phenyl]methanamine hydrochloride (3.67 g) and potassium carbonate (5.29 g) was stirred in ethanol (50 ml) at 85° C. for 24 hr. The reaction mixture was treated with 1N sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=4:1). The obtained yellow solid was dissolved in methanol, and 4N hydrogen chloride-ethyl acetate solution (4 ml) was added. The mixture was crystallized from methanol-ethyl acetate, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (1.22 g).

Workup

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

Sources & evidence

ORD record
ord-361722180ab54c058927bfbe808f420b
Source dataset
uspto-grants-2011_07
Patent number
US07982044B2

Reaction notes

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