Ethyl (chloroformyl)acetate → Ethyl 2-(4-chlorophenyl)-1,3-thiazole-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl formylchloroacetate (1.45 g, 9.6 mmol; obtained according to Panizzi, L. Gazz. Chim.Ital., 1946, 76, 56) and 4-chlorothiobenzamide (1.76 g, 9.6 mmol) in EtOH (50 mL) was refluxed for 48 h. The reaction mixture was then cooled to -20° C. and the solid formed was filtered and dried to give ethyl 2-(4-chlorophenyl)thiazole-5-carboxylate (0.59 g, 23%): mp 144°-145° C.; 1H NMR (300 MHz, CDCl3) δ (TMS) 8.40 (s, 1H, thiazole), 7.92 (dt, Jt =1.8, Jd =8.6, 2H, arom), 7.44 (dt, Jt =1.8, Jd =8.6, 2H, arom), 4.39 (q, J=7, 2H, OCH2), 1.40 (t, J=7, 3H, OCH2CH3). Analysis calculated for C12H10ClNO2S: C 53.84; H 3.76; N 5.23; S 11.97. Found: C 54.22; H 3.52; N 5.25; S 11.46.

Provenance & Evidence