Ethyl bromopyruvate → HCID 19842281, compound

HRID 1638316Notes

Reaction equation

HRID 1638316 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[S:8])[NH2:7].Br[CH2:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:8][CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:7]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 2777138furan-2-carbothioamide

Product 1

HCID 19842281HCID 19842281, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-furan-thiocarboxamide (1.63 g) dissolved in dry ethanol (65 ml) with heating was added ethyl bromopyruvate (1.97 ml) and the mixture was refluxed for 30 minutes. Then the solvent was removed from the reaction mixture, and the residue was treated with water, neutralized with 4% aqueous sodium carbonate and extracted three times with ethyl acetate. The organic layer was washed with saturated aqueous NaCl, dried (anhydrous Na2SO4) and concentrated to give yellowish crystals of ethyl 2-(2-furyl)-4-thiazolecarboxylate (3.12 g).

Workup

  1. temperaturewith heating
  2. temperaturethe mixture was refluxed for 30 minutes
  3. customThen the solvent was removed from the reaction mixture
  4. additionthe residue was treated with water
  5. extractionextracted three times with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous NaCl
  7. dry with materialdried (anhydrous Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0192acb3e34d4d51889bafa6a63cac9f
Source dataset
uspto-grants-1989_11
Patent number
US04879295

Reaction notes

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