Methyl 2-chloroacetoacetate → HCID 53669583, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of methyl 2-chloroacetoacetate (30 g, 0.19 mol) and 4-cyanothiobenzamide (21.5 g, 0.13 mol) in MeOH (250 mL) was refluxed for 15 h. The reaction mixture was then cooled to 0° C., filtered after 20 h and washed with cooled (-20° C.) MeOH and with ether. The resulting off-white solid was dried to give methyl 2-(4-cyanophenyl)-4-methylthiazole-5-carboxylate (18.7 g, 55%). If desired, additional product may be recovered by flash chromatography of the washings: mp 186°-187° C.; 1H NMR (300 MHz, CDCl3) δ (TMS) 8.07 (dt, Jt =1.6, Jd =8.3, 2H, arom), 7.74 (dt, Jt =1.6, Jd =8.3, 2H, arom), 3.91 (s, 3H, OMe), 2.79 (s, 3H, Me-thiazole). Analysis calculated for C13H10N2O2S: C 60.45; H 3.90; N 10.85; S 12.41. Found: C 60.31; H 3.80; N 10.53; S 11.79.

Provenance & Evidence