Ethyl 2-chloroacetoacetate → Ethyl 4-methyl-2-(pyridin-4-yl)-1,3-thiazole-5-carboxylate

HRID 278563Notes

Reaction equation

HRID 278563 reaction equation
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Cl[CH:11]([C:17]([CH3:19])=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[CH3:19][C:17]1[N:9]=[C:1]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[S:8][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 27237884-Pyridinecarbothioamide

Product 1

HCID 619089Ethyl 4-methyl-2-(pyridin-4-yl)-1,3-thiazole-5-carboxylateYield 40.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of thioisonicotinamide (2.76 g) and ethyl 2-chloroacetoacetate (3.6 g) in ethanol (30 ml) was heated for 20 hours under reflux and the solvent was evaporated. To the residue was added saturated sodium hydrogen carbonate solution, and the solution was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was subjected to silica gel chromatography, and eluted with hexane-ethyl acetate (2:1) to give the title compound as crystals (2.0 g, 40.3%).

Workup

  1. temperaturewas heated for 20 hours
  2. temperatureunder reflux
  3. customthe solvent was evaporated
  4. additionTo the residue was added saturated sodium hydrogen carbonate solution
  5. extractionthe solution was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated
  9. washeluted with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-58e6a3ae1dae4acc99823f85c5237a3d
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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