Methanethioamide → 4-(2-Methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 1400175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400175
[CH:1]([NH2:3])=[S:2].[CH2:4]([O:6][C:7](=[O:20])[CH:8](Br)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])=O)[CH3:5]>CCO>[CH2:4]([O:6][C:7]([C:8]1[S:2][CH:1]=[N:3][C:9]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])=[O:20])[CH3:5]

Komponenten

4

Edukt 2

HCID 3005587MethanethioamideHCID 580160512-Bromo-3-(2-methoxyphenyl)-3-oxo-propionic acid ethyl ester

Produkt 1

HCID 670764344-(2-Methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a 0° C. solution of thioformamide (prepared according to Eur. J. Med. Chem. 2004, 39, 867-872) (0.70 g, 11.5 mmol) in absolute EtOH (1 ml) was added a solution of 2-bromo-3-(2-methoxyphenyl)-3-oxo-propionic acid ethyl ester (2.4 g, 7.97 mmol) in ethanol abs. (9 ml) in drops. The reaction mixture was stirred at room temperature for 72 hours. After quenching with water and extraction with chloroform, the organics were dried over Na2SO4 and evaporated. Flash chromatography on SiO2 gel (petroleum ether/ethyl acetate, 60/40) gave crude 4-(2-methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester that was used in the next step without further purification.

Aufarbeitung

  1. customAfter quenching with water and extraction with chloroform
  2. dry with materialthe organics were dried over Na2SO4
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1e5a69bf5c1048e7a337288a698a538d
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906935B2

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