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

HRID 447798

Reaction equation

HRID 447798 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 mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was crystallized from ethanol-diisopropyl ether to give 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 mixture 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. customThe residue was crystallized from ethanol-diisopropyl ether

Sources & evidence

ORD record
ord-cf68c47ef71349c1880e6365e5ca62c0
Source dataset
uspto-grants-2013_07
Patent number
US08481569B2

Linked notes

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