Ethyl 2-chloroacetoacetate → Ethyl 2-(4-Fluorophenyl)-4-methylthiazole-5-carboxylate

HRID 642297Notes

Reaction equation

HRID 642297 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[CH:4][CH:3]=1.[CH2:11]([O:13][C:14](=[O:20])[CH:15](Cl)[C:16](=O)[CH3:17])[CH3:12]>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[S:7][C:6]([C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)=[N:8][C:16]=1[CH3:17])=[O:20])[CH3:12]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 7372234-Fluorothiobenzamide

Product 1

HCID 9079430Ethyl 2-(4-Fluorophenyl)-4-methylthiazole-5-carboxylateYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-fluoro-thiobenzamide (1.25 g, 8.04 mmol) and 2-chloro-3-oxo-butyric acid ethyl ester (1.11 mL, 8.20 mmol) in ethanol (18 mL) was heated at refluxed for 16 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 (1.99 g): MS: (+) m/z 266.03 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat refluxed for 16 h before it
  3. concentrationconcentrated in vacuo
  4. customIt was partitioned between ethyl acetate and saturated sodium bicarbonate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-221ee62980014549bf9cc560bee8d286
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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