Methyl iodide → 1-Methyl-4-nitroimidazole

Temperature

60 °C

To a mixture of 4-nitro-1H-imidazole (2.0 g, 17.7 mmol) and K2CO3 (3.67 g, 26.6 mmol) in acetonitrile (18 mL) was added iodomethane (1.32 mL, 21.2 mmol) and the mixture was heated in a sealed vial at 60° C. overnight. The mixture was filtered washing with acetone. The filtrate was concentrated under reduced pressure, and the residue was diluted with hot isopropanol and cooled, and the precipitated solid was collected by filtration. The solid was dissolved in chloroform and filtered, and the filtrate was concentrated under reduced pressure. The residue was triturated with propan-2-ol and collected by filtration to afford 1-methyl-4-nitro-1H-imidazole (1.03 g, 46%) as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 8.37 (d, J=1.1 Hz, 1H), 7.82 (s, 1H), 3.76 (s, 3H).

1. filtrationThe mixture was filtered
2. washwashing with acetone
3. concentrationThe filtrate was concentrated under reduced pressure
4. additionthe residue was diluted with hot isopropanol
5. temperaturecooled
6. filtrationthe precipitated solid was collected by filtration
7. dissolutionThe solid was dissolved in chloroform
8. filtrationfiltered
9. concentrationthe filtrate was concentrated under reduced pressure
10. customThe residue was triturated with propan-2-ol
11. filtrationcollected by filtration

ORD record

ord-82d090d805044f5994f5badc7d746b75

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633207B2