2-(2-Chlorophenoxy)ethanethioamide → HCID 54014773, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(4-fluorophenyl)-2-(4-methylthiophenyl)-2-bromo-ethanone (2.05 g, 6.04 mmol) (Example 1, Step 3) and 2-chlorophenoxy thioacetamide (1.21 g, 6.0 mmol) in 30 mL of acetonitrile was heated to reflux for 3 hours. The solution was diluted with methanol, cooled to 0° C. in an ice bath and a precipitate formed that was removed by filtration. The crude solid was further purified by flash chromatography over silica gel and the appropriate fractions were combined, concentrated in vacuo and crystallized from methanol to provide 2.60 g (98%) of pure 4-2- ((2 -chlorophenoxy) methyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl) thiazole: mp 126°-129° C., 1H NMR (CDCl3) 300 MHz 7.55-7.39 (m, 4H), 7.28-6.90 (m, 8H), 5.44 (s, 2H), 2.49 (s, 3H). 19F NMR (CDCl3) -114.00 (m). Mass spectrum M+H+ =442.

Provenance & Evidence