Butyl bromide → 1-Butyl-1H-imidazole-4-carboxaldehyde
Reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]1.[H-].[Na+].[CH2:10](Br)[CH2:11][CH2:12][CH3:13].C1OCCOCCOCCOCCOCCOC1.[Cl-].[NH4+]>O1CCCC1>[CH2:10]([N:1]1[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]1)[CH2:11][CH2:12][CH3:13]Participants
Procedure
Imidazole-4-carboxaldehyde (10 g, 104 mmol) was added portionwise to a solution of sodium hydride (4.56 g, 60% dispersion in mineral oil, 114 mmol) in tetrahydrofuran (150 ml), and the solution stirred for 30 minutes. n-Butyl bromide (15.7 g, 114 mmol) was added portionwise, followed by 18-crown-6 (50 mg), and the reaction heated under reflux for 18 hours. Aqueous ammonium chloride solution was added to the cooled reaction and the mixture extracted with ethyl acetate (2×) and dichloromethane (2×). The combined organic extracts were then dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a solvent gradient of pentane:ethyl acetate (50:50 to 25:75), to give the title compound, 4.45 g, 28% yield.
Workup
- temperaturethe reaction heated
- temperatureunder reflux for 18 hours
- extractionthe mixture extracted with ethyl acetate (2×) and dichloromethane (2×)
- dry with materialThe combined organic extracts were then dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel
- washeluting with a solvent gradient of pentane:ethyl acetate (50:50 to 25:75)
Sources & evidence
- ORD record
- ord-31a4ce6a4f664c55b2a42a52fb74345a
- Source dataset
- uspto-grants-2005_09
- Patent number
- US06949577B2
Reaction notes
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