Butyl iodide → 1-Butyl-4-phenyl-1H-imidazole

HRID 1643212Notes

Reaction equation

HRID 1643212 reaction equation
[H-].[Na+].[C:3]1([C:9]2[N:10]=[CH:11][NH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[CH2:15][CH2:16][CH2:17][CH3:18]>CN(C=O)C>[CH2:15]([N:12]1[CH:13]=[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:10]=[CH:11]1)[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 178418822HCID 178418822, compound

Product 1

HCID 184377891-Butyl-4-phenyl-1H-imidazoleYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

To the suspension of sodium hydride (2.40 g, 60% mineral oil suspension, 60 mmol) in 30 ml of anhydrous DMF is added a solution of 4-phenylimidazole (7.21 g, 50 mmol) in 30 ml of DMF at room temperature, the resulting mixture is stirred at 70° C. 1h, and then cooled to room temperature followed by the dropwise addition of iodobutane (9.66 g 52.5 mmol, 1.05 eq.). The mixture is stirred at room temperature for 1 h, heated to 70° C. and stirred for an additional 8 h. The reaction mixture is cooled to room temperature, poured into 200 ml of ice-water, extracted with ethyl acetate (100 ml×3). The combined organics are washed with water, brine, dried over anhydrous sodium sulfate, filtered, evaporated at reduced pressure and purified by flash chromatography on silica gel to obtain 9.08 g of 1-butyl-4-phenylimidazole. 1H NMR (400 MHz, CDCl3) δ 7.77 (2H, d, J=7.6 Hz), 7.49 (1H, s), 7.36 (2H, t, J=7.6 Hz), 7.23 (1H, m), 7.20 (1H, s), 3.95 (2H, t, 17.2 Hz), 1.80 (2H, m), 1.36 (2H, m), 0.96 (3H, t, J=7.2 Hz); MS (+VE) m/z 201 (M+1).

Workup

  1. stirringThe mixture is stirred at room temperature for 1 h
  2. temperatureheated to 70° C.
  3. stirringstirred for an additional 8 h
  4. temperatureThe reaction mixture is cooled to room temperature
  5. extractionextracted with ethyl acetate (100 ml×3)
  6. washThe combined organics are washed with water, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated at reduced pressure
  10. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-929c660af04041c19cc449a11c12dcb3
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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