Urea → Ethyl 2-amino-1,3-oxazole-4-carboxylate

HRID 1526306Notes

Reaction equation

HRID 1526306 reaction equation
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:10][C:11]([NH2:13])=[O:12]>C(O)C>[NH2:13][C:11]1[O:12][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:10]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 66144Ethyl bromopyruvate

Product 1

HCID 319549Ethyl 2-amino-1,3-oxazole-4-carboxylateYield 71.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl bromopyruvate (5.00 g), urea (2.31 g) and ethanol (51 mL) was refluxed overnight. The reaction mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (2.87 g).

Workup

  1. temperaturewas refluxed overnight
  2. customthe solvent was evaporated under reduced pressure
  3. additionTo the residue was added water
  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

Sources & evidence

ORD record
ord-1d03e540ba4445ff9bdf59ebaf1e269c
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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