Dimethylformamide → Methyl 3-(3-cyanopyridin-2-ylthio)propanoate

Participants

Reaction Steps

A mixture of anhydrous N,N-dimethylformamide (30 ml), sodium methoxide (0.54 g, 10 mmol), methyl 3-mercaptopropionate (1.20 g, 10 mmol) and 2-chloro-3-cyanopyridine (1.38 g, 10 mmol) was stirred at room temperature for 1 h. The reaction mixture was poured into water (200 ml), the product filtered, washed with water and recrystallized from ethyl acetate/hexanes to yield methyl 3-(3-cyanopyridin-2-ylthio)propanoate (1.60 g). mp 101-102° C. as heavy colorless prisms. 1H NMR (300 MHz, CDCl3): 8.45 (dd, 1H), 7.02 (dd, 1H), 3.68 (s, 3H), 3.49 (t, 2H), 2.78 ppm (t, 2H).

Provenance & Evidence