Ethyl bromopyruvate → Ethyl 2-(cyanomethyl)-1,3-thiazole-4-carboxylate

HRID 2391161Notes

Reaction equation

HRID 2391161 reaction equation
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:10]([CH2:12][C:13](=[S:15])[NH2:14])#[N:11]>CN(C)C=O>[C:10]([CH2:12][C:13]1[S:15][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:14]=1)#[N:11]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 14162772-Cyanoethanethioamide

Product 1

HCID 801076Ethyl 2-(cyanomethyl)-1,3-thiazole-4-carboxylateYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of ethyl 3-bromo-2-oxopropanate (21 g, 110 mmol) in N,N-dimethylformamide (50 mL) was added a solution of 2-cyanoethanethioamide (10 g, 100 mmol) in N,N-dimethylformamide (50 mL) under ice-cooling, and the reaction mixture was stirred at room temperature for 12 hr. The mixture was concentrated under reduced pressure, and the obtained residue was dissolved in ethyl acetate, and washed with 5% aqueous sodium hydrogencarbonate solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→60/40) to give the title compound (5.1 g, 26%) as a yellow powder.

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe obtained residue was dissolved in ethyl acetate
  4. washwashed with 5% aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltrated
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→60/40)

Sources & evidence

ORD record
ord-9180cbece96543c689a558ba4a4f0479
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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