Dimethylformamide → HCID 86673130, compound

Participants

Reaction Conditions

Reaction Steps

To a solution, cooled to 2-5°C. on an ice bath, of 6.29 g (74.78 mmol) of cyanoacetamide in 140 mL of anhydrous DMF are added portionwise 5.98 g (149.55 mmol) of 60% sodium hydride. The mixture is stirred for 15 minutes at 2-5°C. and this suspension is then added rapidly to the solution of 14.5 g (71.22 mmol) of the acid fluoride prepared in step 2.5 in 155 mL of anhydrous DMF, precooled to 2-5°C. on an ice bath. The mixture is stirred overnight at room temperature and then cooled to 2-5°C., and 2.99 g (74.78 mmol) of 60% sodium hydride are added portionwise. The medium is stirred for 4 hours at room temperature, ice is then added slowly to destroy the excess hydride, and the reaction medium is poured into an ice-water mixture. The resulting mixture is acidified by adding aqueous 0.1 N HCl solution. The precipitate formed is isolated by filtration, rinsed with water and then dried in an oven, followed by rinsing with pentane. 14.0 g of expected product are finally obtained in the form of a pale orange solid. Yield=73.4%.

Provenance & Evidence