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

HRID 2261769Notes

Reaction equation

HRID 2261769 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[S:8])=[CH:5][CH:4]=1.[CH2:12]([O:14][C:15](=[O:21])[CH:16](Cl)[C:17](=O)[CH3:18])[CH3:13]>C(O)C>[CH2:12]([O:14][C:15]([C:16]1[S:8][C:7]([C:6]2[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:9][C:17]=1[CH3:18])=[O:21])[CH3:13]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 7368274-Methoxybenzenecarbothioamide

Product 1

HCID 7540952Ethyl 2-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-methoxy-thiobenzamide (5 g, 30 mmol) and 2-chloro-3-oxo-butyric acid ethyl ester (4.6 mL, 33 mmol) in ethanol is stirred under reflux overnight. The reaction mixture is concentrated and the residue is triturated with ether to give the title compound as a yellow solid (5.8 g, 70%). LC-ES/MS m/e 278 (M+1)

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe reaction mixture is concentrated
  3. customthe residue is triturated with ether

Sources & evidence

ORD record
ord-a3c08cef075445e887fc92290ef207b9
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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