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

HRID 2261774Notes

Reaction equation

HRID 2261774 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-carboxylate

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 triturated with ether to give 2-(4-methoxy-phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester as a yellow solid, 5.8 g (70%). LC-MS: 278 (M+1)

Workup

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

Sources & evidence

ORD record
ord-278cd98664f9404fa803057530dc43e7
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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