1-Bromopropane → 1-Propyl-1H-imidazole-2-carbaldehyde

HRID 445231Notes

Reaction equation

HRID 445231 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].CN1C[CH2:12][CH2:11][C:10]1=O.BrCCC.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:10]([N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7])[CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 249551H-imidazole-2-carbaldehyde

Product 1

HCID 47776601-Propyl-1H-imidazole-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To 1H-imidazole-2-carboaldehyde (800 mg), N-methylpyrrolidone (10 mL) was added, followed by dissolution with heating. To this solution, 1-bromopropane (2.05 g) and potassium carbonate (1.15 g) were added. The reaction solution was stirred at 40° C. for 12 hours. To the reaction solution, water (10 mL) was added. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (dichloromethane) to obtain the title compound (893 mg) having the following physical properties.

Workup

  1. dissolutionfollowed by dissolution
  2. temperaturewith heating
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (dichloromethane)

Sources & evidence

ORD record
ord-994bf3d5af834c759d762f6f2d57f978
Source dataset
uspto-grants-2013_07
Patent number
US08476290B2

Reaction notes

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