Water → 1-[2-(2,4-Dichlorophenyl)hexyl]-4-nitro-1H-imidazole

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Reaction Steps

To 1.3 g (0.0307 mole) of sodium hydroxide in 150 ml of methanol is added 3.5 g (0.0307 mole) of 4-nitroimidazole, and the solution is heated and the methanol distilled off. To the concentrate is added 100 ml of dimethyl formamide and the solution is heated up to 120° to remove the excess methanol and water. This dimethyl formamide solution is then cooled to less than 90° and 10.0 g (of 0.0307 mole) of 2-(2,4-dichlorophenyl)hexyl methane sulfonate is added. The reaction mixture is heated up to 145° for two hours and then cooled and poured into water. The organic material is extracted out with ether and after drying, the extract is stripped to give 11.2 g of residue. The concentrate is triturated with hexane and then dissolved in 25 ml of methanol. The methanol solution is poured slowly into water and a gummy solid forms. This solid is separated by filtration, dried and recrystallized from acetone-hexane to give 4.2 g (41 %) of the product, m.p. 67°-9°.

Provenance & Evidence