Potassium Carbonate → HCID 66970077, compound

HRID 1015853Notes

Reaction equation

HRID 1015853 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.[CH2:16]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[CH2:28][NH2:29])(=[O:20])=[O:19])[CH3:17].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:29]([CH2:28][C:22]2[CH:23]=[C:24]([CH3:27])[CH:25]=[CH:26][C:21]=2[S:18]([CH2:16][CH3:17])(=[O:20])=[O:19])[CH:10]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 66877852HCID 66877852, compound

Product 1

HCID 66970077HCID 66970077, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(Step 4) 2-Cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (2.35 g), 1-[2-(ethylsulfonyl)-5-methylphenyl]methanamine hydrochloride obtained in Step 3 (3.0 g) and potassium carbonate (4.15 g) were stirred in ethanol (30 ml) at 85° C. for 20 hr. The reaction mixture was treated with 1N sodium hydroxide solution, and extracted with a mixed solvent of ethyl acetate-tetrahydrofuran. 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=7:3). The obtained residue 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 (0.55 g).

Workup

  1. extractionextracted with a mixed solvent of ethyl acetate-tetrahydrofuran
  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=7:3)
  6. dissolutionThe obtained residue 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-e200631fc4d9443fa3452bb7ccb103db
Source dataset
uspto-grants-2011_07
Patent number
US07985863B2

Reaction notes

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