Synthetic Route of 2469-99-0,Some common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, molecular formula is C4H5NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
(v) 2-Cyano-N-[5-(4-(1,1-dimethylethyl)phenyl)thien-2-yl]-3-hydroxybut-2-enamide A suspension of cyanoacetone, sodium salt (40.98 g); in freshly sodium dried and distilled tetrahydrofuran (200 ml) was mechanically stirred and cooled in an ice-bath. A slightly turbid solution of 2-[4-(1,1-dimethylethyl)phenyl]-5-isocyanatothiophene (100 g), in dry tetrahydrofuran (400 ml) was added dropwise during 40 minutes at 3-5 C. After stirring the mustard coloured suspension in the ice-bath for a further 20 minutes, the bath was then removed, stirring continued for 52 minutes at ambient temperature, then for 1.5 hours at 55 +-2 C. in a heating mantle. After evaporation in vacuo the residual cream coloured paste was stirred in 0.7 N sodium hydroxide (975 ml) for 30 minutes. Filtration removed an insoluble cream coloured solid. The alkaline filtrate was adjusted to pH 1 by the addition of concentrated hydrochloric acid, precipitating a cream coloured pasty solid which was removed by filtration, washed with water (approximately 3 1) and partially dried at 60 C. in vacuo. This solid was stirred at reflux in absolute ethanol (2 1) for 15 minutes, then for 45 minutes in an ice-bath. After filtration, washing with ice-cold ethanol (400 ml) and drying at 60 C. in vacuo. It was further purified by stirring for 10 minutes with charcoal (5 g) in boiling ethyl acetate (2.25 1). The charcoal was removed by filtration and washed on the filter with hot ethyl acetate (300 ml). The filtrate and washings were combined and reduced in volume by 1.5 1 by evaporating in vacuo. After standing in an ice-bath for 1 hour, pale green crystals were removed by filtration, washed with 40-60 C. petrol (100 ml) and dried at 45 C. in vacuo. The crystalline solid was finally purified by stirring in 1N sodium hydroxide (750 ml) and ether (750 ml). The lower aqueous alkaline layer was removed and filtered to clarify. Concentrated hydrochloric acid was added to adjust to pH 1. The resulting cream coloured precipitated solid was filtered off, washed on the filter with water (2 1) and dried at 60 C. in vacuo, m.p. 226-228 C.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Oxobutanenitrile, its application will become more common.
Reference:
Patent; Lilly Industries Limited; US4983619; (1991); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts