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

HRID 457380Notes

Reaction equation

HRID 457380 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. 1 h, 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, J=7.2 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. temperature1 h, and then cooled to room temperature
  2. stirringThe mixture is stirred at room temperature for 1 h
  3. temperatureheated to 70° C.
  4. stirringstirred for an additional 8 h
  5. temperatureThe reaction mixture is cooled to room temperature
  6. extractionextracted with ethyl acetate (100 ml×3)
  7. washThe combined organics are washed with water, brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated at reduced pressure
  11. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-681e2beecd57418bb854d41fd064bcee
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

Loading…