Methyl iodide → 2-Methyl-5-(3-nitrophenyl)-2H-tetrazole

Participants

Reaction Steps

3-Nitro-(1H-tetrazol-5-yl)benzene (0.99 g) was added at 0° C. to a magnetically stirred suspension of sodium hydride (243 mg, 60% oil dispersion) in 50 ml of dry tetrahydrofuran. The reaction mixture was stirred for 15 minutes and then iodomethane was added in 6 increments of 0.5 ml over a 3 hour period. The reaction mixture was concentrated in vacuo and the residue was partitioned between water (50 ml) and ethyl acetate. The aqueous layer was extracted (2×15 ml) with ethyl acetate and the combined organic extracts were washed with brine, dried, and concentrated. The title compound was obtained as a solid after flash chromatography on silica gel (chloroform-methanol, 95:5).

Provenance & Evidence