1-Bromopropane → 1-Propyl-1H-imidazole-4-carbaldehyde

HRID 497561Notes

Reaction equation

HRID 497561 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

7

Reactant 5

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2855718-Crown-6HCID 764281H-Imidazole-4-carbaldehyde

Product 1

HCID 103517661-Propyl-1H-imidazole-4-carbaldehydeYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 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 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 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.

Workup

  1. temperaturethe reaction heated
  2. temperatureunder reflux for 18 hours
  3. extractionthe mixture extracted with ethyl acetate (2×) and dichloromethane (2×)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel
  8. washeluting with ethyl acetate:pentane (40:60)

Sources & evidence

ORD record
ord-8cf29040bed84b98a19b753ffed96407
Source dataset
uspto-grants-2005_09
Patent number
US06949577B2

Reaction notes

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