p-Toluenesulfonic acid → 2-Nitro-1-(oxan-2-yl)-1H-imidazole

Participants

Reaction Steps

A suspension of 0.113 g (1.0 mmol) of 2-nitroimidazole and 10 ml of 2,3-dihydropyran was stirred at 80° C. in the presence of 5 mg of p-toluenesulfonic acid for 1 hr. according to the procedure of Robins et al. [J. Am. Chem. Soc 83, 2574 (1961)]. The excess of 2,3-dihydropyran was removed under reduced pressure. The residue was chromatographed on silica gel by elution with ethyl acetate-benzene mixture (employing a gradient from 9:1 to 1:1) to provide 0.165 g (83.7%) of the title compound, which was recrystallized from petroleum ether, mp 50° C.

Provenance & Evidence