Sulfuric Acid → 3-(2-Chloro-phenyl)-3-oxo-propionamide

HRID 1667659

Reaction equation

HRID 1667659 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:12])[CH2:9][C:10]#[N:11].S(=O)(=O)(O)[OH:14]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:12])[CH2:9][C:10]([NH2:11])=[O:14]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 27342012-Chlorobenzoylacetonitrile

Product 1

HCID 866427963-(2-Chloro-phenyl)-3-oxo-propionamide

Procedure

A mixture of 17.0 g (94.65 mmole) of 3-(2-chloro-phenyl)-3-oxo-propionitrile and 50 mL of sulfuric acid was stirred at room temperature for 18 hours. The mixture was poured into ice-water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium carbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate-hexanes (gradient 20:80-70:30) to give 14.12 g of 3-(2-chloro-phenyl)-3-oxo-propionamide.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic phases were washed with saturated aqueous sodium carbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with ethyl acetate-hexanes (gradient 20:80-70:30)

Sources & evidence

ORD record
ord-1c03274c4acb49079d28150685097457
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Linked notes

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