Hydrochloric Acid → HCID 89717682, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-cyanoacetamide (0.888 g, 10.56 mmol) in DMF (2.268 mL) was added to a suspension of sodium hydride 60% wt. in mineral oil (0.443 g, 11.08 mmol) in DMF (5.67 mL) to give a grey suspension. After cooling to 0° C. (Note: Hydrogen Gas evolution) the resulting mixture was stirred at 0° C. for 30 minutes. Then a solution of 5-(4-fluoro-3-nitrophenyl)-2-methyl-2H-tetrazole (1.15 g, 5.15 mmol) in DMF (2.3 mL) was added to give a deep purple solution. After 3 hours, the reaction mixture was slowly poured into an ice-water mixture (33.0 mL) and conc.HCl (0.952 mL). The resulting yellow slurry was stirred for 30 minutes, the solid was filtered, washed with water (3×5 mL) and then with Hexane (2×5 mL), dried at 40° C. under high vacuum until constant weight to give 2-cyano-2-(4-(2-methyl-2H-tetrazol-5-yl)-2-nitrophenyl)acetamide (1.41 g, 95% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 4.49 (s, 3H) 5.77 (s, 1H) 7.77 (s, 1H) 7.95 (d, J=8.2 Hz, 1H) 8.03 (s, 1H) 8.51 (dd, J=8.2, 1.8 Hz, 1H) 8.70 (d, J=1.8 Hz, 1H); MS m/z 288.1 (M+H)+; HPLC 96.4% @ 220 nm, RT=1.31 minutes.

Provenance & Evidence