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

HRID 642307

Reaktionsgleichung

Reaktionsgleichung von HRID 642307
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([NH2:5])=[S:4].[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:4][C:3]([N:2]([CH3:1])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[N:5][C:17]=1[CH3:18])=[O:21])[CH3:13]

Komponenten

4

Edukt 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 7236311-Methyl-1-phenylthiourea

Produkt 1

HCID 130483514-Methyl-2-(methyl-phenyl-amino)-thiazole-5-carboxylic acid ethyl esterAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-methyl-1-phenyl-thiourea (5.03 g, 30.3 mmol) and 2-chloro-3-oxo-butyric acid ethyl ester (4.4 mL, 31.8 mmol) in ethanol (18 mL) was refluxed for 20 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 brown solid (7.39 g): MS: (+) m/z 277.0 (M+1).

Aufarbeitung

  1. temperaturewas refluxed for 20 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-1f86698936034ec39ec323144c124c42
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

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