Iodine → HCID 18437784, compound

HRID 1375371Notes

Reaction equation

HRID 1375371 reaction equation
[Li]CCCC.[CH2:6]([N:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]=[CH:11]1)[CH2:7][CH2:8][CH3:9].[I:21]I.[NH4+].[Cl-]>CCCCCC.C1COCC1>[CH2:6]([N:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]=[C:11]1[I:21])[CH2:7][CH2:8][CH3:9]

Participants

7

Reactant 4

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

Product 1

HCID 18437784HCID 18437784, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

BuLi (1.60 g) in hexane is added to a solution of 1-butyl-4-phenyl-1H-imidazole (4.16 g) in 60 mL of THF. The mixture is stirred at −78° C. for 1 hour. A solution of I2 (5.81 g) in 20 mL of THF is then added dropwise. The resulting mixture is stirred at −78° C. for 30 minutes and then warmed to room temperature. Saturated NH4Cl is added to quench the reaction. The THF is evaporated; the residue is extracted with ethyl acetate, washed with brine, and dried over Na2SO4. Concentration and purification via flash chromatography provides 1-butyl-2-iodo-4-phenyl-1H-imidazole.

Workup

  1. stirringThe resulting mixture is stirred at −78° C. for 30 minutes
  2. temperaturewarmed to room temperature
  3. customto quench
  4. customthe reaction
  5. customThe THF is evaporated
  6. extractionthe residue is extracted with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationConcentration and purification via flash chromatography

Sources & evidence

ORD record
ord-0624f87e780e4e0bbd058bc3173cbb6b
Source dataset
uspto-grants-2007_01
Patent number
US07169775B2

Reaction notes

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