Iodine → HCID 66757302, compound

HRID 1643213Notes

Reaction equation

HRID 1643213 reaction equation
C([N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=[CH:6]1)CCC.[CH2:16]([Li])[CH2:17][CH2:18][CH3:19].CCCCCC.[I:27]I.[Cl-].[NH4+]>C1COCC1>[CH2:16]([C:9]1[NH:5][C:6]([I:27])=[N:7][C:8]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 5

HCID 807IodineHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 184377891-Butyl-4-phenyl-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 66757302HCID 66757302, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-butyl-4-phenylimidazole (4.0 g, 20 mmol) in 60 ml of anhydrous THF at −78° C. under nitrogen is added a solution of n-butyllithium in hexane (1.6M, 13.13 ml, 21 mmol, 1.05 eq.) dropwise. The resulting mixture is stirred at −78° C. for 1 h followed by dropwise addition of a solution of iodine (5.33 g, 21 mmol, 1.05 eq.) in 40 ml of THF. The resulting solution is stirred at −78° C. for 30 min. and then warmed to room temperature. Saturated ammonium chloride (30 mL) is added to quench the reaction. The resulting mixture is evaporated a reduced pressure to remove THF, extracted with ethyl acetate, washed with water and brine, dried over Na2-SO4, filtered and evaporated. Purification by silica gel chromatography (hexanes/ethyl acetate, from 8:1 to 5:1) affords 5.73 g of butyl-2-iodo-4-phenylimidazole. 1H NMR (400 MHz, CDCl3) δ 7.73 (2H, dd, J=1.2, 8.4 Hz), 7.36 (2H, m), 7.30 (1H, s), 7.24 (1H, m), 3.91 (2H, t, J=7.2 Hz), 179 (2H, m), 1.41 (2H, m), 0.98 (3H, t, J=7.2Hz); MS (+VE) m/z 327 (M+1).

Workup

  1. stirringThe resulting solution is stirred at −78° C. for 30 min.
  2. temperaturewarmed to room temperature
  3. customto quench
  4. customthe reaction
  5. customThe resulting mixture is evaporated a reduced pressure
  6. customto remove THF
  7. extractionextracted with ethyl acetate
  8. washwashed with water and brine
  9. dry with materialdried over Na2-SO4
  10. filtrationfiltered
  11. customevaporated
  12. customPurification by silica gel chromatography (hexanes/ethyl acetate, from 8:1 to 5:1)

Sources & evidence

ORD record
ord-9e69feb8b06447eabd220495d9f384f1
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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