Methyl iodide → 2-methyl-5-(4-nitrophenyl)-2H-tetrazole

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 60% NaH (0.116 g, 2.89 mmol) and MeI (0.196 mL, 3.15 mmol) in DMF (2 mL) (cooled to 0° C., under N2) is added dropwise, a solution of 5-(4-nitrophenyl)-1H-tetrazole (0.502, 2.63 mmol) in DMF (7 mL). The reaction mixture is stirred under N2 for 1 hour and 30 min at 5° C. and then quenched with water and extracted with EtOAc. The organic layers are combined and washed with sat. NaCl, dried over MgSO4, filtered and evaporated to give a residue purified by silica gel column chromatography. Elution with 80:20 followed by 60:40 petroleum ether-EtOAc affords 2-methyl-5-(4-nitro-phenyl)-2H-tetrazole (0.265 g, 49%) as a white solid and 1-methyl-5-(4-nitro-phenyl)-1H-tetrazole (37.7 mg, 7%) as a yellow solid. The isomers are identified by NOE experiments.

Provenance & Evidence