2-Chlorothiobenzamide → 2-(2-Chlorophenyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylthiophenyl)ethanone (2.03 g, 5.98 mmol) (Example 1, Step 3) in acetonitrile (60mL) in a 125 mL round bottom flask was added 2-chlorothiobenzamide (1.08 g, 6.28 mmol) and the suspension heated to 80° C. for 4 hours. The reaction was cooled to room temperature and the suspension filtered through a fritted funnel. The solid was recrystallized from hot acetonitrile (50 mL) and methanol (150 mL) yielding 2-(2-chlorophenyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole as a tan solid (1.23 g, 50 %): mp 133°-134° C. 1H NMR (CDCl3) 300 mHz δ8.37 (d, J=6.17 Hz, 1H), 7.60 (dd, J=8.68, 5.28, 2H) 7.51 (d, J=9.44 Hz, 1H), 7.32-7.42 (m, 2H), 7.32 (d, J=8.68 Hz, 2H), 7.21 (d, J=8.68 Hz, 2H), 7.02 (t, J=8.68, 2H), 2.51 (s, 3H). MS (EI): m/z 412 (MH+).

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