Potassium Hydroxide → HCID 13670762, compound

HRID 963108Notes

Reaction equation

HRID 963108 reaction equation
[NH2:1][C:2]1[S:6][C:5]([CH2:7][CH:8](C(OCC)=O)[C:9]([O:11]CC)=[O:10])=[CH:4][C:3]=1[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26].[OH-].[K+]>C(O)C>[NH2:1][C:2]1[S:6][C:5]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13670761HCID 13670761, compound

Product 1

HCID 13670762HCID 13670762, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Diethyl 2-(5-amino-4-(2-chlorobenzoyl)thiophen-2-ylmethyl)malonate (20 g) and a 4M potassium hydroxide aqueous solution (30 ml) were added to ethanol (120 ml), and the mixture was refluxed under heating for 2 hours. The solvent was evaporated, and the residue was dissolved in water. 1.2M Hydrochloric acid was added to adjust the solution to pH 3. The mixture was extracted with ethyl acetate to give a product and the product was washed with brine, and dried over magnesium sulfate. The solvent was evaporated. Dimethylformamide (30 ml) and toluene (70 ml) were added to the residue, and the mixture was heated at 80° C. for 1 hour. The mixture was washed with water, dried over magnesium sulfate and concentrated to give 11.0 g of 3-(5-amino-4-(2-chlorobenzoyl)thiophen-2-yl)propionic acid.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hours
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in water
  5. addition1.2M Hydrochloric acid was added
  6. extractionThe mixture was extracted with ethyl acetate
  7. customto give a product
  8. washthe product was washed with brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was evaporated
  11. additionDimethylformamide (30 ml) and toluene (70 ml) were added to the residue
  12. washThe mixture was washed with water
  13. dry with materialdried over magnesium sulfate
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-dda8c155d1e849e49345540008f7efe7
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

Loading…