Trimethylsilyl cyanide → HCID 117925974, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,3-Dihydrobenzo[de]isochromen-1-ol (100 mg) in acetonitrile (3 mL) at 0° C. was added Zn(II)iodide (86 mg) and suspension was stirred at 0° C. for 10 minutes. Trimethylsilyl cyanide (672 μL) was added and the reaction mixture was stirred at room temperature overnight. Solution of saturated NaHCO3 (10 mL) was added and the mixture was extracted with ethyl acetate (2×15 mL). Combined organic phases were washed with brine and dried with Na2SO4. Evaporation of solvents afforded 110 mg 1,3-dihydrobenzo[de]isochromene-1-carbonitrile that was mixed with ethylene diamine mono-p-toluenesulfonic acid salt (157 mg) and the mixture was heated to 200° C. After 3 hours the reaction mixture was cooled to room temperature and taken to mixture of dichloromethane (10 ml) and aqueous NaHCO3 (1:1 saturated solution/water). Phases were separated and aqueous phase was extracted with dichloromethane (5 mL). Combined organic phases were dried with Na2SO4 and concentrated. The evaporation residue was purified by separation method E (aq.NH3-MeOH-dichloromethane). The obtained 2-(1,3-dihydrobenzo[de]isochromen-1-yl)-4,5-dihydro-1H-imidazole was converted to the title compound using salt formation method A.

Provenance & Evidence