Hydrogen Peroxide → 1-Benzyl-5-hydroxymethyl-1H-imidazole

Temperature

40 °C

1-Benzyl-2-mercapto-5-hydroxymethylimidazole(2.2 g, 9.99 mmol) and tungstic acid(H2WO4, 25 mg, 1 mol %) were mixed in 11 ml of methanol. The mixture was warmed to 40° C. in a water bath and 30% hydrogen peroxide(3.75 g, 3.2 molar eq.) was added dropwise thereto for 5 minutes while stirring. The reaction mixture was warmed to 65° C. and refluxed, and stirred at the same temperature for 2.5 hours. Upon exhaustion of the starting material, the mixture was cooled in an ice bath and thereto was added 1 N sodium hydroxide solution(18 ml) to adjust pH of the mixture to 10. The resulting solid was further stirred for 15 minutes, filtered, washed twice with 15 ml of distilled water and 15 ml of isopropyl ether, respectively, and dried to give 1.3 g(Yield 69%, HPLC purity 96.7%) of the title compound as a white powder.

1. temperatureThe reaction mixture was warmed to 65° C.
2. temperaturerefluxed
3. stirringstirred at the same temperature for 2.5 hours
4. temperatureUpon exhaustion of the starting material, the mixture was cooled in an ice bath
5. stirringThe resulting solid was further stirred for 15 minutes
6. filtrationfiltered
7. washwashed twice with 15 ml of distilled water and 15 ml of isopropyl ether
8. customrespectively, and dried

ORD record

ord-f1c09490d0594e029258e665f2465a76

Source dataset

uspto-grants-2003_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06630593B1