Methyl iodide → HCID 90251302, compound

Temperature

-78 °C

13.07 g (38.62 mmol) of rac-2-[(diphenylmethylene)amino]-4,4-difluorobutanonitrile from Example 67A were initially charged in 255 ml of abs. THF, and 15.6 ml (39.0 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 10 min. Subsequently, 22.6 g (154.46 mmol) of iodomethane were added to the reaction solution at −78° C. The reaction mixture was gradually brought to 0° C. over 3.5 h. After complete depletion of the starting material, the reaction solution was quenched with water at 0° C., ethyl acetate was added and the mixture was washed twice with saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulphate, filtered and concentrated by rotary evaporation. The residue was purified by means of silica gel chromatography (eluent:cyclohexane/ethyl acetate=15/1). 11.4 g of the target compound were obtained (91% of theory, 92% purity).

1. waitThe reaction mixture was gradually brought to 0° C. over 3.5 h
2. customAfter complete depletion of the starting material, the reaction solution was quenched with water at 0° C.
3. additionethyl acetate was added
4. washthe mixture was washed twice with saturated aqueous sodium chloride solution
5. dry with materialThe organic phase was dried over sodium sulphate
6. filtrationfiltered
7. concentrationconcentrated by rotary evaporation
8. customThe residue was purified by means of silica gel chromatography (eluent:cyclohexane/ethyl acetate=15/1)

ORD record

ord-ef9967a023b545cbb9db5de20dbe0ed1

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422285B2