Methyl iodide → HCID 70676804, compound

Temperature

0 °C

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).

1. customthe resulting reaction mixture
2. stirringwas stirred at room temperature for 2 h
3. customAfter this time, the reaction was quenched by water (20 mL) at 0° C.
4. concentrationconcentrated under reduced pressure
5. additionThe residue was diluted with dichloromethane (100 mL)
6. washIt was then washed with brine
7. dry with materialdried over anhydrous Na2SO4
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica-gel column chromatography
10. washeluting with 6:1 petroleum ether/ethyl acetate

ORD record

ord-226c1067cfa14eaba8cbf1052d668a74

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08754077B2