Imidazole → HCID 68842558, compound

HRID 660692Notes

Reaction equation

HRID 660692 reaction equation
N1C=CN=C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[I:25]I.[C:27]1([S:33]([CH2:36][CH2:37][CH2:38][CH2:39]O)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl.O>[I:25][CH2:39][CH2:38][CH2:37][CH2:36][S:33]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:35])=[O:34]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 122775654-Benzenesulfonylbutan-1-ol

Product 1

HCID 68842558HCID 68842558, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of imidazole (1.4 g, 20.5 mmol) in CH2Cl2 (20 mL) is added PPh3 (5.4 g, 20.5 mmol). The solution is cooled to 0° C. and iodine (5.2 g, 20.5 mmol) is added in 2 portions. The mixture is allowed to warm to RT then 4-benzenesulfonylbutan-1-ol is added and the mixture is stirred at RT for 24 h. The mixture is diluted with water and extracted with EtOAc (3×). The organic layer is washed with a 20% solution of Na2S2O3 and dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue purified by flash chromatography using hexane/EtOAc (1:1) as eluent to give the title compound as a white solid.

Workup

  1. temperatureto warm to RT
  2. extractionextracted with EtOAc (3×)
  3. washThe organic layer is washed with a 20% solution of Na2S2O3
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-7d532b2b93b44d339285ce827e436658
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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