Ethyl 2-chloroacetoacetate → Ethyl 2-ethyl-4-methyl-1,3-thiazole-5-carboxylate

HRID 1058350Notes

Reaction equation

HRID 1058350 reaction equation
Cl[CH:2]([C:8]([CH3:10])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:11]([NH2:15])(=[S:14])[CH2:12][CH3:13]>C(O)C>[CH2:6]([O:5][C:3]([C:2]1[S:14][C:11]([CH2:12][CH3:13])=[N:15][C:8]=1[CH3:10])=[O:4])[CH3:7]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 2760628Propanethioamide

Product 1

HCID 23560693Ethyl 2-ethyl-4-methyl-1,3-thiazole-5-carboxylateYield 81.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-chloroacetoacetate (2.00 g, 10.04 mmol) and thiopropionamide (1.00 g, 11.22 mmol) in ethanol (100 mL) was heated at reflux overnight. The solvent was evaporated and dichloromethane (100 mL) added. The solution was washed with water (2×100 mL) and brine (100 mL), dried (MgSO4), filtered, evaporated and the concentrate was chromatographed over silica gel (10% ethyl acetate/hexanes) to give 2-ethyl-4-methylthiazole-5-carboxylic acid ethyl ester (1.63 g, 81% yield) as a colorless liquid.

Workup

  1. temperatureat reflux overnight
  2. customThe solvent was evaporated
  3. additiondichloromethane (100 mL) added
  4. washThe solution was washed with water (2×100 mL) and brine (100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customthe concentrate was chromatographed over silica gel (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b83915895e264ac5ae4bcc8fa8f3e220
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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