2-Cyanoethanethioamide → HCID 54466438, compound

Participants

Reaction Steps

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (Example 26, Step 2) (0.249 g, 0.734 mmol) in ethanol (9 mL) in a 25 mL round bottom flask was added 2-cyanothioacetamide (0.077 g, 0.771 mmol) and the solution heated to reflux for 14 hours. The reaction was cooled to room temperature, was was concentrated in vacuo and the residue dissolved in ethyl acetate. This solution was washed successively with Na2CO3 (10% solution) and brine, dried over Na2SO4, filtered and reconcentrated in vacuo yielding an orange crystalline solid. This solid was purified by flash chromatography (4:1 hexane:ethyl acetate ) yielding 2-(cyanomethyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole as very fine pink crystals (0.090 g, 36%): mp 118°-119° C. 1H NMR (CDCl3) 400 mHz δ7.50 (d, J=5.38, 2H), 7.47 (d, J=5.38, 2H), 7.24-7.18 (m, 4H), 7.00 (t, J=8.80, 2H), 4.16 (s, 2H), 2.50 (s, 3H). MS (EI): m/z 340 (M+). HRMS Δ=2.7 mmu.

Provenance & Evidence