Hydrogen Peroxide → 1-(3-Hydroxypropyl)-5-hydroxymethylimidazole

Temperature

40 °C

1-(3-Hydroxypropyl)-2-mercapto-5-hydroxymethylimidazole(5.0 g, 23.1 mmol) and tungstic acid(H2WO4, 58 mg, 1 mol %) were mixed in 25 ml of methanol and 25 ml of distilled water. The mixture was warmed to 40° C. and 3.6 g of 30% hydrogen peroxide was added dropwise thereto. The whole mixture was stirred for 15 minutes and cooled and then, neutralized with 1 N sodium hydroxide solution. The resulting mixture was extracted twice with 25 ml of n-butanol and the solvent was distilled under reduced pressure to give 3.45 g(Yield 80.7%) of the title compound. 1H NMR (500 MHz, CDCl3) δ 7.46 (1H, s), 6.91 (1H, s), 4.61 (2H, s), 4.15 (2H, t, J=7 Hz), 3.52 (2H, t, J=7 Hz), 2.01 (2H, m).

1. temperaturecooled
2. extractionThe resulting mixture was extracted twice with 25 ml of n-butanol
3. distillationthe solvent was distilled under reduced pressure

ORD record

ord-8e9566bc6dcb4904b94cfead5e15585a

Source dataset

uspto-grants-2003_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06630593B1