Dimethylformamide → 5-Benzothiazolecarbonitrile

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Into a mixture of 5-bromo-1,3-benzothiazole (300 mg, 1.40 mmol, 1.00 equiv) and zinc cyanide (131.6 mg, 0.80 equiv) in N,N-dimethylformamide (6.0 mL) was added Pd(PPh3)4 (80.9 mg, 0.07 mmol, 0.05 equiv) and nitrogen was bubbled for 5 min. The resulting mixture was heated overnight at 80° C., quenched by water (15.0 mL), and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with brine (2×15 mL) and dried over Na2SO4. After filtered and concentrated under reduced pressure, the residue was purified by flash chromatography on silica gel, eluting with a mixture of 5-10% ethyl acetate in petroleum ether to afford the title compound as a light yellow solid. MS m/z [M+H]+ (ESI): 161.

Herkunft & Nachweise