Nitric Acid → (1-(propan-2-yl)-1H-imidazol-5-yl)methanol

To 5.0M nitric acid (81 ml) was added sodium nitrite (248 mg), and 5-hydroxymethyl-1-isopropyl-2-mercaptoimidazole (15.5 g) was added by portions at 0° C. The mixture was allowed to be at room temperature and the mixture was stirred for 2 hours, and water (100 ml) was added to the mixture. The mixture was neutralized with potassium carbonate at 0° C., and the solvent was distilled off under reduced pressure. Ethanol was added to the mixture, and the insolubles were filtered off, and the solvent was distilled off under reduced pressure. To the obtained residue was added methanol-ethyl acetate, and basic silica gel was added to the mixture. This mixture was purified by basic silica gel column chromatography (methanol-ethyl acetate=1:8) to obtain solid, which was recrystallized from diisopropyl ether-ethyl acetate, to give 5-hydroxymethyl-1-isopropylimidazole (4.84 g) as brown crystals.

1. additionwas added by portions at 0° C
2. customto be at room temperature
3. distillationthe solvent was distilled off under reduced pressure
4. additionEthanol was added to the mixture
5. filtrationthe insolubles were filtered off
6. distillationthe solvent was distilled off under reduced pressure
7. additionTo the obtained residue was added methanol-ethyl acetate, and basic silica gel
8. additionwas added to the mixture
9. customThis mixture was purified by basic silica gel column chromatography (methanol-ethyl acetate=1:8)
10. customto obtain solid, which
11. customwas recrystallized from diisopropyl ether-ethyl acetate

ORD record

ord-f6153d017802488b96f15165070c7c34

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262185B2