Methanol → Methyl 1-hexylimidazole-5-carboxylate

Imidazole-5-carboxylic acid (10.0 g, 89 mmol) was dissolved in methanol (185 ml) and concentrated sulphuric acid (10 ml) was added dropwise. The mixture was heated under reflux for two days. After cooling in ice and neutralising with dilute sodium hydroxide solution the solvents were removed by evaporation. The white solid produced was suspended in methanol (70 ml) and hexyl iodide (26.3 ml, 178 mmol) in methanol (30 ml) was added. After heating under reflux overnight, the mixture was cooled and filtered through a pad of diatomaceous earth, washing well with methanol. The filtrate was concentrated and the residue purified by column chromatography, eluting with 1.5% methanol/dichloromethane (v/v), to give methyl 1-hexylimidazole-5-carboxylate (1.4 g; 7.5% yield), as an oil;

1. temperatureThe mixture was heated
2. temperatureunder reflux for two days
3. temperatureAfter cooling in ice
4. customneutralising with dilute sodium hydroxide solution the solvents were removed by evaporation
5. customThe white solid produced
6. temperatureAfter heating
7. temperatureunder reflux overnight
8. temperaturethe mixture was cooled
9. filtrationfiltered through a pad of diatomaceous earth
10. washwashing well with methanol
11. concentrationThe filtrate was concentrated
12. customthe residue purified by column chromatography
13. washeluting with 1.5% methanol/dichloromethane (v/v)

ORD 기록

ord-02980b4c483840b08d49ba23e693bf23

출처 데이터셋

uspto-grants-1995_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05410064