Chloroacetone → Ethyl 4-methyl-1,3-thiazole-2-carboxylate

HRID 1889048

Reaction equation

HRID 1889048 reaction equation
[NH2:1][C:2](=[S:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl[CH2:10][C:11](=O)[CH3:12]>C(O)C>[CH3:12][C:11]1[N:1]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[S:8][CH:10]=1

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 2733398Ethyl thiooxamate

Product 1

HCID 567306Ethyl 4-methyl-1,3-thiazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl amino(thioxo)acetate (500 mg, 3.75 mmol) in ethanol (9.387 ml) was stirred at room temperature under an atmosphere of argon. 1-Chloro-2-propanone (0.299 ml, 3.75 mmol) was added and the solution was heated to reflux for 48 hours. The solution was allowed to cool to room temperature and then it was concentrated under reduced pressure to give a yellow coloured oily solid. The residue was chromatographed [SiO2, 0-100% EtOAc in Hexane] to give a yellow coloured oil identified as product in 208 mg.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 48 hours
  3. concentrationit was concentrated under reduced pressure
  4. customto give a yellow coloured oily solid
  5. customThe residue was chromatographed [SiO2, 0-100% EtOAc in Hexane]
  6. customto give a yellow coloured oil

Sources & evidence

ORD record
ord-6c668f6c9e7f4e829153cb521dd36bea
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Linked notes

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