Methyl iodide → HCID 70676804, compound

Participants

Reaction Conditions

Reaction Steps

To a 100-mL single-neck round-bottomed containing 4-nitro-2H-1,2,3-triazole (2.0 g, 17.5 mmol) and THF (10 mL) at 0° C. was added NaH (1.7 g, 35.0 mmol, 2.0 eq.). The mixture was stirred at 0° C. for 15 min. A solution of CH3I (3.68 g, 26.3 mmol, 1.5 eq.) in acetone (40 mL) was added and the resulting reaction mixture was stirred at room temperature for 2 h. After this time, the reaction was quenched by water (20 mL) at 0° C. and concentrated under reduced pressure. The residue was diluted with dichloromethane (100 mL). It was then washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 6:1 petroleum ether/ethyl acetate to afford 1-methyl-5-nitro-1H-1,2,3-triazole (1.34 g, 60%) as a white solid and 149a (800 mg, 35%) as a slightly yellow solid. 1H NMR (500 MHz, CDCl3) δ 8.34 (s, 1H), 4.26 (s, 3H). 1-Methyl-5-nitro-1H-1,2,3-triazole: 1H NMR (500 MHz, CDCl3) δ 8.16 (s, 1H), 4.31 (s, 3H).

Provenance & Evidence