Ethyl bromopyruvate → Ethyl 2-pyridin-2-yl-1,3-thiazole-4-carboxylate

HRID 1871032Notes

Reaction equation

HRID 1871032 reaction equation
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](=[S:18])[NH2:17]>C(O)C>[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[S:18][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:17]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 1549499Pyridine-2-carbothioamide

Product 1

HCID 10082761Ethyl 2-pyridin-2-yl-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

16.3 ml of ethyl bromopyruvate were added dropwise to 15.9 g of the product of Stage B in 250 ml of ethanol and the mixture was refluxed for 5 hours. The solvent was evaporated under reduced pressure and the residue was chromatographed on silica (eluant: hexane-AcOEt 1-1) to obtain 10.2 g of the expected product melting at 69.1° C.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was chromatographed on silica (eluant: hexane-AcOEt 1-1)

Sources & evidence

ORD record
ord-49f8b9933fcf4a94af540d1776f1b1b1
Source dataset
uspto-grants-2000_08
Patent number
US06100404

Reaction notes

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