Ethyl bromopyruvate → Ethyl 2-ethyl-1,3-thiazole-4-carboxylate

HRID 2390544Notes

Reaction equation

HRID 2390544 reaction equation
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:10](=[S:14])([NH2:13])[CH2:11][CH3:12]>C(O)C>[CH2:11]([C:10]1[S:14][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:13]=1)[CH3:12]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 2760628Propanethioamide

Product 1

HCID 15056276Ethyl 2-ethyl-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-bromo-2-oxopropanoate (4.10 mL, 32.67 mmol) was added dropwise over 10 min to a stirred solution of propanethioamide (3 g, 33.65 mmol) in ethanol (40 mL) cooled in an ice bath. After 16 h the reaction mixture was evaporated in vacuo. Purification was by silica gel chromatography eluting with EtOAc:iso-hexanes, 1:3 to give the sub-title compound as a yellow oil. Yield: 2.78 g

Workup

  1. temperaturecooled in an ice bath
  2. customAfter 16 h the reaction mixture was evaporated in vacuo
  3. customPurification
  4. washeluting with EtOAc

Sources & evidence

ORD record
ord-a2016dbc73054a85a204793783074cae
Source dataset
uspto-grants-2012_09
Patent number
US08273774B2

Reaction notes

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