Methyl iodide → 1-Methyl-4-nitroimidazole

To a mixture of 4-nitro-1H-imidazole (2.0 g, 17.7 mmol) and K2CO3 (3.67 g, 26.5 mmol) in acetonitrile (20 mL) was added iodomethane (1.3 mL, 3.0 g, 21.2 mmol) dropwise while stirring at room temperature. The resulting mixture was stirred at 60° C. overnight. It was then evaporated under reduced pressure and the residue was diluted with water (20 mL). The mixture was extracted with dichloromethane (2×20 mL). The combined extract was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 100:1 dichloromethane/methanol to afford 268a as a yellow solid (1.8 g, 82%). MS-ESI: [M+H]+ 128.1. 1H NMR (500 MHz, DMSO-d6) δ 8.37 (s, 1H), 7.82 (s, 1H), 3.76 (s, 3H).

1. stirringThe resulting mixture was stirred at 60° C. overnight
2. customIt was then evaporated under reduced pressure
3. additionthe residue was diluted with water (20 mL)
4. extractionThe mixture was extracted with dichloromethane (2×20 mL)
5. extractionThe combined extract
6. concentrationwas concentrated under reduced pressure
7. customthe residue was purified by silica-gel column chromatography
8. washeluting with 100:1 dichloromethane/methanol

ORD-Eintrag

ord-bf3bea0a127a4f6a873d385550f9b673

Quelldatensatz

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08716274B2