Ethyl bromopyruvate → 2-(N-Carbethoxy-N-methylamino)methyl-4-carbethoxythiazole

HRID 1702259Notes

Reaction equation

HRID 1702259 reaction equation
[C:1]([N:6]([CH2:8][C:9]([NH2:11])=[S:10])[CH3:7])([O:3][CH2:4][CH3:5])=[O:2].Br[CH2:13][C:14](=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C>[C:1]([N:6]([CH2:8][C:9]1[S:10][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:11]=1)[CH3:7])([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 13125119(N-Carbethoxy-N-methylamino)thioacetamide

Product 1

HCID 204021112-(N-Carbethoxy-N-methylamino)methyl-4-carbethoxythiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of (N-carbethoxy-N-methylamino)thioacetamide (30.7 g; 0.17 mole) [prepared in Step B] in 180 ml of absolute ethanol was added a solution of ethyl bromopyruvate (25.0 ml; 0.20 mole) in 130 ml of absolute ethanol. The reaction mixture was heated at reflux temperature for 17 hours and then evaporated under reduced pressure, and the residue was partitioned between ether and water. The organic layer was washed with water and saturated sodium chloride solution, dried, filtered and evaporated under reduced pressure to give an oil which was placed on silica gel and chromatographed using diethyl ether as the eluting solvent. The appropriate fractions yielded the title compound as an oil; TLC [Silica/CH2Cl2 :CH3CN (85.15)] gave Rf=0.50. The NMR spectrum (60 MHz) in d6 dimethyl sulfoxide gave the following resonances δ: 8.49 (s, 1H); 4.79 (s, 2H); 4.23 (m, 4H); 3.00 (s, 3H); 1.30 (q, 6H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 17 hours
  3. customevaporated under reduced pressure
  4. customthe residue was partitioned between ether and water
  5. washThe organic layer was washed with water and saturated sodium chloride solution
  6. customdried
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto give an oil which
  10. customchromatographed

Sources & evidence

ORD record
ord-2a97b9005a0b4af79c78e1344e81b0f1
Source dataset
uspto-grants-1983_04
Patent number
US04380638

Reaction notes

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