N,N'-Dimethylethylenediamine → 2,5-Dimethylbenzonitrile

Temperature

110 °C

An oven dried screw cap test tube was charged with NaCN (93 mg, 1.898 mmol), dried KI (52 mg, 0.313 mmol, 20 mol %) and CuI (30 mg, 0.158 mmol, 10 mol %), evacuated and backfilled with argon three times. 2-Bromo-1,4-dimethylbenzene (215 μL, 1.557 mmol), N,N′-dimethylethylenediamine (165 μL, 1.549 mmol) and anhydrous toluene (1 mL) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 24 h. The resulting yellow suspension was cooled to room temperature, 2 mL of ethyl acetate, 1 mL of ammonium hydroxide (30%) and 1 mL of water were added. The mixture was stirred at 25° C. for 10 min, then the organic layer was washed with 1 mL of water and dried over MgSO4. The GC analysis showed consumption of the majority of the starting material, and formation of the title compound (as confirmed by GC-MS).

1. customAn oven dried screw
2. customcap test tube
3. customevacuated
4. customThe tube was sealed
5. temperatureThe resulting yellow suspension was cooled to room temperature
6. stirringThe mixture was stirred at 25° C. for 10 min
7. washthe organic layer was washed with 1 mL of water
8. dry with materialdried over MgSO4
9. customconsumption of the majority of the starting material, and formation of the title compound (as confirmed by GC-MS)

ORD record

ord-9d54b481f12c4a0ea6714bbb3aa7e5a1

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06888032B2