Diiodomethane → 2-[1-(4-bromobenzyl)vinyl]-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 425429Notes

Reaction equation

HRID 425429 reaction equation
C[Si](Cl)(C)C.[Pb](I)I.I[CH2:10]I.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([C:22]2[N:23]([S:32]([N:35]([CH3:37])[CH3:36])(=[O:34])=[O:33])[CH:24]=[C:25]([CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[N:26]=2)=O)=[CH:15][CH:14]=1>O1CCCC1.[Zn].Cl[Ti](Cl)(Cl)Cl>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([C:22]2[N:23]([S:32]([N:35]([CH3:37])[CH3:36])(=[O:34])=[O:33])[CH:24]=[C:25]([CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[N:26]=2)=[CH2:10])=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 6346DiiodomethaneHCID 6397ChlorotrimethylsilaneHCID 24931Lead iodideHCID 591403972-[(4-bromophenyl)acetyl]-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

Product 1

HCID 667056182-[1-(4-bromobenzyl)vinyl]-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

TMSCl (0.1 mL) was added to a suspension of zinc (1.2 g, 18.3 mmol) and lead (II) iodide in tetrahydrofuran at room temperature. After stirring at room temperature for 10 min, diiodomethane (0.653 mL) was added dropwise maintaining the reaction at a gentle reflux. After stirring 1 h, the reaction mixture was cooled to 0° C., TiCl4 (1 M in DCM) (2.02 mL) was added dropwise. After stirring at room temperature for 1 h, a solution of intermediate 7 (238 mg, 0.54 mmol) in tetrahydrofuran was added and the reaction monitored by LCMS. The reaction mixture was quenched with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The combined organics were washed with brine, dried (sodium sulfate) and concentrated in vacuo to afford 2-[1-(4-bromobenzyl)vinyl]-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide which was used in the subsequent step without further purification.

Workup

  1. temperaturemaintaining
  2. customthe reaction at a gentle reflux
  3. stirringAfter stirring 1 h
  4. temperaturethe reaction mixture was cooled to 0° C.
  5. stirringAfter stirring at room temperature for 1 h
  6. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  7. extractionextracted with ethyl acetate
  8. washThe combined organics were washed with brine
  9. dry with materialdried (sodium sulfate)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee412b072288485f8fea982921688d0c
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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