Sodium Iodide → HCID 178420497, compound

Participants

Reaction Steps

5-Phenyl-4-(phenylhydrazono)-4H-pyrazol-3-ylamine (65 mg, 0.25 mmol) was dissolved in 5 mL of acetonitrile. Potassium carbonate (70 mg, 0.5 mmol) and a catalytic amount of sodium iodide were added and the solution was heated to reflux. 4-(2-chloroethyl)morpholine hyrdochloride (50 mg, 0.25 mmol) was added in small portions over 30 min. After heating at reflux for 6 hours, the reaction was allowed to cool to ambient temperature and was stirred overnight. Some of the residual 4-(2-chloroethyl)morpholine was removed by stirring the solution over 50 mg of polystyrene bound thiophenol with 1 drop of diethylisopropylamine. The solution was filtered through celite and evaporated to a tan solid. The solid was then dissolved in ethyl acetate and precipitated with hexanes. The solid was isolated by filtration and air dried. The material was purified by column chromatography (CH2Cl2:MeOH=10:1) to yield two fractions in amounts of 28 mg and 35 mg (total 67%). 1H NMR (ppm, 200 MHz, CDCl3) δ 2.60 (t, 4H), 2.80 (t, 2H), 3.70 (t, 4H), 4.18 (t, 2H), 7.25-7.50 (m, 8H), 7.78 (d, 2H), 8.15 (d, 2H).

Provenance & Evidence