Ethyl bromopyruvate → Ethyl 2-isopropylthiazole-4-carboxylate

HRID 1174208Notes

Reaction equation

HRID 1174208 reaction equation
[CH3:1][CH:2]([CH3:6])[C:3](=[S:5])[NH2:4].Br[CH2:8][C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C(O)C>[CH:2]([C:3]1[S:5][CH:8]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:4]=1)([CH3:6])[CH3:1]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 109095072-Methylpropanethioamide

Product 1

HCID 10535999Ethyl 2-isopropylthiazole-4-carboxylateYield 108.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution containing the product from Example 56A (8.6 g, 83.5 mmol) in ethanol (250 mL) was treated with ethyl bromopyruvate (12.6 mL, 100 mmol), and the mixture was heated at 70° C. for 3 hours, cooled to 25° C., concentrated, and partitioned between dichloromethane and saturated NaHCO3. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated to give the title compound (18 g, 57% yield), which was used without further purification.

Workup

  1. temperaturecooled to 25° C.
  2. concentrationconcentrated
  3. custompartitioned between dichloromethane and saturated NaHCO3
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0d8fb291c7c048559548fc0fcd047f67
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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