Ethyl bromopyruvate → Ethyl 2-(4-chlorophenyl)-1,3-thiazole-4-carboxylate
Reaktionsgleichung
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[S:16])=[CH:13][CH:12]=1>CCO>[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]2[S:16][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:17]=2)=[CH:13][CH:12]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of ethyl bromopyruvate (354 mg, 1.8 mmol) and 4-chlorothiobenzamide (283 g, 1.65 mmol) in EtOH (40 mL) was refluxed for 3 h. The mixture was evaporated to dryness and the resulting oil was purified by flash chromatography to give ethyl 2-(4-chlorophenyl)thiazole-4-carboxylate as a colourless oil: 1H NMR (80 MHz, CDCl3) δ (TMS) 8.15 (s, 1H, thiazole), 7.95 (dt, Jt =2, Jd =8.5, 2H, arom), 7.42 (dt, Jt =2, Jd =8.5, 2H, arom), 4.45 (q, J=7, 2H, OCH2), 1.43 (t, J=7, 3H, OCH2CH3). Analysis calculated for C12H10ClNO2S: C 53.84; H 3.76; N 5.23; S 11.97. Found: C 53.65; H 3.77; N 5.23; S 11.51.