Ethyl 2-chloroacetoacetate → Ethyl 4-Methyl-2-(3-methoxyphenyl)thiazole-5-carboxylate

HRID 642341Notes

Reaction equation

HRID 642341 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH2:8])=[S:7].[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:7][C:6]([C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)=[N:8][C:17]=1[CH3:18])=[O:21])[CH3:13]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 20608383-Methoxybenzene-1-carbothioamide

Product 1

HCID 50997800Ethyl 4-Methyl-2-(3-methoxyphenyl)thiazole-5-carboxylateYield 91.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-methoxy-thiobenzamide (1.99 g, 11.88 mmole) and 2-chloro-3-oxo-butyric acid ethyl ester (1.7 ml, 12.11 mmole) in ethanol (20 ml) was refluxed for 18 h before it was cooled to room temperature and concentrated in vacuo. It was partitioned between ethyl acetate and saturated sodium bicarbonate, the organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (3.02 g). MS: (+) m/z 277.93 (M+1).

Workup

  1. temperaturewas refluxed for 18 h before it
  2. concentrationconcentrated in vacuo
  3. customIt was partitioned between ethyl acetate and saturated sodium bicarbonate
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbb1f714676843f1a73e427c19a664e9
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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