[(Diphenylmethylene)amino]acetonitrile → HCID 117858306, compound

Temperature

-78 °C

18 g (81.72 mmol) of [(diphenylmethylene)amino]acetonitrile were initially charged in 500 ml of abs. THF, and 39.22 ml (98.06 mmol) of n-butyllithium (2.5 N in hexane) were added at −78° C. under argon, and the mixture was stirred at −78° C. for a further 15 min. Subsequently, the reaction solution was warmed up to 0° C. and 16.9 g (89.89 mmol) of 1-fluoro-3-iodopropane were added dropwise to the reaction solution, which was stirred at 0° C. for a further 15 min. The reaction solution was quenched with water at 0° C., ethyl acetate was added and the mixture was washed with saturated aqueous sodium chloride solution. The aqueous phase was reextracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated by rotary evaporation. The residue was purified by means of silica gel chromatography (eluent: 100% toluene, post-purification with dichloromethane/cyclohexane=1/1 to 2/1). A total of 16.73 g of the target compound (73% of theory) were obtained.

1. temperatureSubsequently, the reaction solution was warmed up to 0° C.
2. stirringwas stirred at 0° C. for a further 15 min
3. customThe reaction solution was quenched with water at 0° C.
4. additionethyl acetate was added
5. washthe mixture was washed with saturated aqueous sodium chloride solution
6. dry with materialThe combined organic phases were dried over sodium sulphate
7. filtrationfiltered
8. concentrationconcentrated by rotary evaporation
9. customThe residue was purified by means of silica gel chromatography (eluent: 100% toluene, post-purification with dichloromethane/cyclohexane=1/1 to 2/1)

ORD record

ord-f20beaa87bb7437cbf04a94791518abd

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422285B2