Imidazole → HCID 68843147, compound

HRID 660748Notes

Reaction equation

HRID 660748 reaction equation
[I:1]I.N1C=CN=C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:27]1([CH2:33][S:34]([CH2:37][CH2:38][CH2:39][CH2:40]O)(=[O:36])=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[I:1][CH2:40][CH2:39][CH2:38][CH2:37][S:34]([CH2:33][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 68839757HCID 68839757, compound

Product 1

HCID 68843147HCID 68843147, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of iodine (1.2 g, 4.5 mmol), imidazole (0.34 g, 4.4 mmol) and Ph3P (1.2 g, 4.4 mmol) in methylene chloride (10 mL) is added 4-phenylmethanesulfonylbutan-1-ol (0.99 g, 4.34 mmol) and the mixture is stirred at RT for 1 h. The mixture is filtered and the filtrate evaporated. The resulting oil is dissolved in EtOAc and washed with saturated sodium thiosulfate and brine. The organic phase is dried over magnesium sulfate and the solvent removed under reduced pressure. The resulting solid is washed with ether and the filtrate is evaporated to give the title compound as a white solid.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate evaporated
  3. dissolutionThe resulting oil is dissolved in EtOAc
  4. washwashed with saturated sodium thiosulfate and brine
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customthe solvent removed under reduced pressure
  7. washThe resulting solid is washed with ether
  8. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-f5086f71cf74411ab157d18114fd9b78
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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