4-(Trifluoromethyl)thiobenzamide → [5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]acetic acid ethyl ester

HRID 253204

Reaktionsgleichung

Reaktionsgleichung von HRID 253204
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C:9](=[S:11])[NH2:10])=[CH:5][CH:4]=1.[CH2:14]([O:16][C:17](=[O:24])[CH2:18][C:19](=O)[CH:20](Br)[CH3:21])[CH3:15]>C(O)C>[CH2:14]([O:16][C:17](=[O:24])[CH2:18][C:19]1[N:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:12])([F:1])[F:13])=[CH:4][CH:5]=2)[S:11][C:20]=1[CH3:21])[CH3:15]

Komponenten

4

Edukt 2

HCID 27348234-(Trifluoromethyl)thiobenzamideHCID 12780443Ethyl 4-bromo-3-oxopentanoate

Produkt 1

HCID 57986743[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]acetic acid ethyl esterAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

To a solution of 4-trifluoromethyl-benzene-thioamide (1.845 g, 9 mmol) in ethanol (15 mL, 200 proof) add ethyl-4-bromo-3-oxo-pentanoate (2.07 g, 9 mmol). Seal this solution warm the solution to 170° C. in a Personal Chemistry™ microwave oven and stir at this temperature for 20 min. Cool the resulting solution to room temperature, concentrate under reduced pressure and purify the residue by flash chromatography (elute with 30% ethyl acetate/10% dichloromethane in heptane) and obtain the title compound as a white solid (1.4 g). MS (ESI) m/z 330 (M+H); H1 NMR (CDCl3) δ1.87 (bs, 1H), 2.49 (s, 3H), 4.86 (s, 2H), 7.67 (d, J=8 Hz, 2H), 8.02 (d, J=8 Hz, 2H).

Aufarbeitung

  1. customSeal this solution
  2. temperatureCool the resulting solution to room temperature
  3. concentrationconcentrate under reduced pressure
  4. custompurify the residue
  5. washby flash chromatography (elute with 30% ethyl acetate/10% dichloromethane in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-b0bd6ebe0ead4b828c3e19bf2a6e5885
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872032B2

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