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

HRID 642297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642297
[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]

Komponenten

4

Edukt 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 7372234-Fluorothiobenzamide

Produkt 1

HCID 9079430Ethyl 2-(4-Fluorophenyl)-4-methylthiazole-5-carboxylateAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-221ee62980014549bf9cc560bee8d286
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

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