Methyl iodide → 1H-Imidazole, 5-((3,5-dichlorophenyl)methyl)-1,2-dimethyl-4-(1-methylethyl)-

In 20 ml of dry acetone was dissolved 930 mg (3.3 mmol) of 5-(3,5-dichlorobenzyl)-4-isopropyl-2-methyl-1H-imidazole (54), followed by addition of 1.4 g (10.1 mmol)of anhydrous potassium carbonate, and the mixture was stirred at room temperature. After 5 minutes, 225 μl (3.6 mmol)of methyl iodide was added at room temperature, and the mixture was heated to 80° C. After 5 hours, the mixture was cooled to room temperature, filtered, and the filtrate was concentrated under reduced pressure. The residue was diluted with water, and extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography (ethyl acetate)to give 218 mg of the target compound (Compound I-100)(yield 22%).

1. temperaturethe mixture was heated to 80° C
2. waitAfter 5 hours
3. temperaturethe mixture was cooled to room temperature
4. filtrationfiltered
5. concentrationthe filtrate was concentrated under reduced pressure
6. additionThe residue was diluted with water
7. extractionextracted with chloroform
8. washThe extract was washed with saturated brine
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationfiltered
11. concentrationthe filtrate was concentrated under reduced pressure
12. customThe crude product was purified by silica gel chromatography (ethyl acetate)to

ORD record

ord-999d3898a7014b6ab6f2004fa9dead13

Source dataset

uspto-grants-1999_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05910506