Acrylonitrile → 3-[4-(1H-Benzoimidazol-2-yl)-furazan-3-ylamino]-propionitrile

Participants

Reaction Steps

To an ice-cooled, stirred solution of 18.2 g of 4-(1H-benzoimidazol-2-yl)-furazan-3-ylamine (90.5 mmol, 1 eq) in 240 ml of pyridine are added 30 ml of sodium methoxide solution (30% in MeOH) (163 mmol, 1.8 eq) and subsequently 6 ml of acrylonitrile (90.5 mmol, 1 eq). The reaction mixture is stirred at room temperature overnight, before it is concentrated under reduced pressure. The residue is suspended in 250 ml of water and extracted with 4×400 ml of ethyl acetate. The combined organic layers are washed with 2×500 ml of brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product is dissolved in about 1000 ml of refluxing ethyl acetate. Then 1700 ml of n-hexane are added to the solution. The resulting turbid mixture is allowed to stand at room temperature overnight and the formed precipitate is filtered to provide 11.1 g of the product as light yellow solid. The filtrate is concentrated to dryness under reduced pressure and the residue is suspended in 100 ml of a 1/1 mixture of n-hexane/ethyl acetate. The suspension is filtered to provide 4.7 g additional product.

Provenance & Evidence