Ethyl 2-chloroacetoacetate → Ethyl 2,4-dimethylthiazole-5-carboxylate

HRID 1661061Notes

Reaction equation

HRID 1661061 reaction equation
Cl[CH:2]([C:8]([CH3:10])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:11]([NH2:14])(=[S:13])[CH3:12]>C(O)C>[CH3:12][C:11]1[S:13][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([CH3:10])[N:14]=1

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 2723949Thioacetamide

Product 1

HCID 603810Ethyl 2,4-dimethylthiazole-5-carboxylateYield 83.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

The mixture of ethyl 2-chloroacetoacetate (111.2 g, 0.68 mol) and thioacetamide (40 g, 0.68 mol) in 150 ml ethanol was heated to 90° C. and stirred for 5 h. After cooling to room temperature, the solvent was removed under vacuum to afford the title compound (105 g, y=83%).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-81d9aaf067124251a646d203f09f0e99
Source dataset
uspto-grants-2011_10
Patent number
US08030322B2

Reaction notes

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