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レコード

ord-ccce70faddf24b1aa6c2236363b886a1

出典データセット

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09238655B2