Sodium Hydroxide → 1-methyl-5-(3-nitrophenyl)-1H-Tetrazole

Participants

Reaction Conditions

Reaction Steps

N-Methyl-3-nitro-benzamide (30.0 g, 167 mmol) was dissolved in acetonitrile (835 mL). Upon dissolution, sodium azide (10.9 g, 167 mmol) was added. The mixture was cooled in an ice bath, and trifluoromethanesulfonic anhydride (29 mL, 172 mmol) was added dropwise at a rate to maintain the reaction temperature below 3° C. The reaction mixture was stirred for 3.5 hours at 0° C. and then poured into 1N aqueous sodium hydroxide (100 mL). The organic layer was separated, dried over sodium sulfate and concentrated under vacuum to 50 mL. The solution was diluted with dichloromethane and water was added. The resuling precipitate was isolated by filtration to give a yellow solid (18.46 g, 54%). The filtrate was concentrated in vacuo and added to boiling ethyl acetate to give a second crop of crystals. Upon cooling to 0° C., additional material (6.07 g, 18%) was isolated by filtration. 1H NMR (300 MHz, CDCl3), δ8.67 (m, 1H), 8.49 (dd, J=8, 2 Hz, 1H), 8.31 (d, J=8 Hz, 1H), 7.94 (dd, J=8, 8 Hz, 1H), 4.22 (s, 3H).

Provenance & Evidence