Cyanogen Bromide → [(3-Ethylphenyl)amino]carbonitrile

Temperature

24 °C

A solution of cyanogen bromide (11.36 g, 107 mmol) in anhydrous diethylether (50 mL) was added slowly to a stirred solution of 3-ethylaniline (20.8 g, 171 mmol) in diethylether at 4° C. After the addition, the reaction mixture was stirred at 24° C. for 12 hours and it became a brown solution with a white precipitate. The precipitate was filtered off; the filtrate was washed with aqueous HCl (1N, 3×150 mL) and brine (60 mL). Then the etherate solution was dried over MgSO4, filtered, and concentrated to yield a thick liquid. The crude product was further purified by chromatography (SiO2, hexanes, hexanes/CH2Cl2, CH2Cl2) to afford 3-ethylphenylcyanamide (11.6 g, 76% in yield) as a liquid.

1. additionAfter the addition
2. filtrationThe precipitate was filtered off
3. washthe filtrate was washed with aqueous HCl (1N, 3×150 mL) and brine (60 mL)
4. dry with materialThen the etherate solution was dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto yield a thick liquid
8. customThe crude product was further purified by chromatography (SiO2, hexanes, hexanes/CH2Cl2, CH2Cl2)

ORD record

ord-3ecec37910c54bdeb68aaa68b0fd6810

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06147063