p-Fluoronitrobenzene → HCID 18543946, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[2-(phenyl)-1,3,4-thiadiazol-5-yl]-1H-imidazole (0.285 g, 1.25 mmol), 1-fluoro-4-nitrobenzene (0.176 g, 1.25 mmol) and sodium carbonate (0.265 g, 2.50 mmol) in DMF (10 mL) was heated at 120° C. for 24 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate and washed with water and brine. The combined organic fraction was dried (Na2SO4) and evaporated to dryness. The crude product was purified by chromatography on silica gel using hexane/ethyl acetate as an eluant to give the product (0.38 g, 87%) as a white solid; 1H NMR δ (DMSO-d6) 8.38 (2H, d, J=8.9 Hz), 7.98 (2H, dd, J=7.7, 1.6 Hz), 7.86 (2H, dd, J=8.8, 1.6 Hz), 7.81 (1H, s), 7.55 (3H, m), 7.43 (1H, dd, J=1.3 Hz); 13C NMR δ (DMSO-d6) 167.8, 159.1, 147.3, 142.6, 136.6, 131.6, 131.0, 129.5, 129.0, 128.1, 127.7, 126.2, 124.3; MS (m/z): 350.4 (M+, 100%).

Provenance & Evidence