Methanol → Methyl 1-hexyl-1H-imidazole-5-carboxylate
Reaction equation
[NH:1]1[C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=[CH:2]1.S(=O)(=O)(O)O.[CH2:14](I)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[CH3:21]O>>[CH2:14]([N:1]1[C:5]([C:6]([O:8][CH3:21])=[O:7])=[CH:4][N:3]=[CH:2]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]Participants
Procedure
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;
Workup
- temperatureThe mixture was heated
- temperatureunder reflux for two days
- temperatureAfter cooling in ice
- customneutralising with dilute sodium hydroxide solution the solvents were removed by evaporation
- customThe white solid produced
- temperatureAfter heating
- temperatureunder reflux overnight
- temperaturethe mixture was cooled
- filtrationfiltered through a pad of diatomaceous earth
- washwashing well with methanol
- concentrationThe filtrate was concentrated
- customthe residue purified by column chromatography
- washeluting with 1.5% methanol/dichloromethane (v/v)
Sources & evidence
- ORD record
- ord-02980b4c483840b08d49ba23e693bf23
- Source dataset
- uspto-grants-1995_04
- Patent number
- US05410064
Reaction notes
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