Hydrochloric Acid → 2-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamide

HRID 1260844Notes

Reaction equation

HRID 1260844 reaction equation
[C:1]([OH:9])(=O)/[C:2](=[C:4](\[CH:6]=[O:7])/[Cl:5])/[Cl:3].[C:10]([CH2:12][C:13]([NH2:15])=[O:14])#[N:11].[OH-].[Na+].Cl>CO>[C:10]([CH:12]([CH:1]1[C:2]([Cl:3])=[C:4]([Cl:5])[C:6](=[O:7])[O:9]1)[C:13]([NH2:15])=[O:14])#[N:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7898CyanoacetamideHCID 14798Sodium HydroxideHCID 2771871Mucochloric Acid

Product 1

HCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideYield 17.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Mucochloric acid (15.1 g) and 2-cyanoacetamide (7.53 g) were dissolved in methanol (53.6 ml), and 2.5N aqueous sodium hydroxide solution (53.6 ml) was added dropwise with stirring under ice-cooling. The mixture was allowed to warm to room temperature and further stirred at room temperature for 3 hr. The reaction mixture was poured into 1N hydrochloric acid containing ice water, methanol was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Crystallization from ethanol-diisopropyl ether gave the title compound (3.74 g) as pale-brown crystals.

Workup

  1. temperaturecooling
  2. stirringfurther stirred at room temperature for 3 hr
  3. customwas evaporated under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customCrystallization from ethanol-diisopropyl ether

Sources & evidence

ORD record
ord-ce3be655126c4ec49088c67aa881aaf1
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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