Isopropyl iodide → 5-Chloro-2-isopropyl 4-nitrobenzotriazole

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Reaction Steps

To a hot, stirred solution (50° C.) of 20.0 grams of 5-chloro-4-nitrobenzotriazole in 600 milliliters of acetonitrile is added 4.2 grams of sodium hydroxide pels and 20.0 grams of isopropyl iodide. The solution is then heated to reflux for 30 hours, filtered and the solvent removed by evaporation to yield an oil. The oil is extracted with concentrated hydrochloric acid (3×200 milliliters) and the resulting solid is collected, washed with water and air dried to yield 15.0 grams (63%) of crude 5-chloro-2-isopropyl 4-nitrobenzotriazole, m.p. 67°-70° C. The analytical sample is recrystallized from n-hexane and has a m.p. 75°-76° C.

Provenance & Evidence