Trimethylsilyl cyanide → HCID 117925974, compound

Temperature

0 °C

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.

1. stirringthe reaction mixture was stirred at room temperature overnight
2. extractionthe mixture was extracted with ethyl acetate (2×15 mL)
3. washCombined organic phases were washed with brine
4. dry with materialdried with Na2SO4
5. customEvaporation of solvents

ORD record

ord-b5412e442c5a47f4af5e7955725a8669

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249127B2