Ethyl 2-chloroacetoacetate → 4-Methyl-2-(4-phenoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 642332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642332
[O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[S:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20](=[O:26])[CH:21](Cl)[C:22](=O)[CH3:23])[CH3:18]>C(O)C>[CH2:17]([O:19][C:20]([C:21]1[S:13][C:12]([C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:16][CH:15]=2)=[N:14][C:22]=1[CH3:23])=[O:26])[CH3:18]

Komponenten

4

Edukt 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 27603534-Phenoxythiobenzamide

Produkt 1

HCID 684263914-Methyl-2-(4-phenoxy-phenyl)-thiazole-5-carboxylic acid ethyl esterAusbeute 93,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4-phenoxy-thiobenzamide (1.02 g, 4.43 mmole) and 2-chloro-3-oxo-butyric acid ethyl ester (625 μl, 4.52 mmole) in ethanol (15 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 (1.41 g). MS: (+) m/z 340.07 (M+1).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0a1c49b6df3d4afdb6b0eb3c591cc126
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

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