Ethyl 2-chloroacetoacetate → Ethyl 2-anilino-4-methyl-1,3-thiazole-5-carboxylate

HRID 642311

Reaktionsgleichung

Reaktionsgleichung von HRID 642311
[C:1]1([NH:7][C:8]([NH2:10])=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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:9][C:8]([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:10][C:16]=1[CH3:17])=[O:20])[CH3:12]

Komponenten

4

Edukt 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 676454Phenylthiourea

Produkt 1

HCID 807772Ethyl 2-anilino-4-methyl-1,3-thiazole-5-carboxylateAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of phenylthiourea (5.04 g, 33.1 mmol) and 2-chloro-3-oxo-butyric acid ethyl ester (4.8 mL, 34.8 mmol) in ethanol (50 mL) was refluxed for 19 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 (8.18 g): MS: (+) m/z 263.0 (M+1).

Aufarbeitung

  1. temperaturewas refluxed for 19 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

Quellen und Nachweise

ORD-Eintrag
ord-23aa6f1f39d544a784f68fdab31785e9
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

Verknüpfte Notizen

Wird geladen…