Reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]1.[H-].[Na+].[CH3:10][CH2:11][CH2:12]Br.C1OCCOCCOCCOCCOCCOC1.[Cl-].[NH4+]>O1CCCC1>[CH2:10]([N:1]1[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]1)[CH2:11][CH3:12]Participants
Procedure
Imidazole-4-carboxaldehyde (30 g, 0.31 mol) was added portionwise to a solution of sodium hydride (13.9 g, 60% dispersion in mineral oil, 0.348 mol) in tetrahydrofuran (450 ml), and the solution was stirred for 45 minutes. n-Propyl bromide (31.2 ml, 0.344 mol) was then added portionwise, followed by 18-crown-6 (150 mg), and the mixture was heated under reflux for 18 hours. Aqueous ammonium chloride solution was added to the cooled solution, and the mixture was extracted with ethyl acetate (2×) and dichloromethane (2×). The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate: pentane (40:60), to give the title compound, 20.2 g, 47% yield. 1H-NMR (DMSO-d6, 400 MHz) δ: 0.80 (t, 3H), 1.76 (m, 2H), 3.98 (t, 2H), 7.84 (s, 1H), 8.04 (s, 1H), 9.70 (s, 1H). LRMS: m/z (TSP+) 277.3 [2M+H]+
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 18 hours
- extractionthe mixture was extracted with ethyl acetate (2×) and dichloromethane (2×)
- dry with materialThe combined organic extracts were dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by column chromatography on silica gel
- washeluting with ethyl acetate: pentane (40:60)
Sources & evidence
- ORD record
- ord-81713f3831ec431895fbb267489a2c43
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06713496B2
Linked notes
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