Water → 1-[4-(2-Azidoethyl)phenyl]-3,5-dimethyl-4-phenyl-1H-pyrazole

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-[4-(2-chloroethyl)phenyl]-3,5-dimethyl-4-phenyl-1H-pyrazole (step 1, 0.34 mmol) and KI (56 mg, 0.34 mmol) in N,N-dimethylformamide (2.7 mL) was added sodium azide (44 mg, 0.68 mmol), and then the resulting mixture was stirred for 6 h at 100° C. The reaction mixture was poured into water (100 mL), and extracted with ethyl acetate/toluene (4:1). The organic layer was washed with water (50 mL) and brine (50 mL), then dried (Na2SO4). After removal of the solvent, the crude product was purified by TLC with hexane/ethyl acetate (1:1) to afford 87 mg (81%) of the title compound as yellow oil: 1H-NMR (CDCl3) δ 7.46-7.29 (9H, m), 3.55 (2H, t, J=7.3 Hz), 2.96 (2H, t, J=7.1 Hz), 2.34 (3H, s), 2.30 (3H, s).

Provenance & Evidence