Benzyl Bromide → HCID 10195506, compound

HRID 1167289Notes

Reaction equation

HRID 1167289 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[NH:11][C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[OH:26])=[N:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:33]([O:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:10]1[NH:9][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:11]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 7498Benzyl Bromide2×HCID 11430Potassium Carbonate2×HCID 135546617HCID 135546617, compound

Product 1

HCID 10195506HCID 10195506, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-[4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazol-2-yl]-phenol (30 mg, 0.0783 mmol) in 3 mL of ethanol were added potassium carbonate (16 mg, 0.117 mmol), benzyl bromide (11 μL, 0.0940 mmol) and tetrabutylammonium iodide (3 mg, 0.1 mmol). The reaction mixture was heated at gentle reflux for 54 h. Additional benzyl bromide (11 μL) and potassium carbonate (16 mg) were added after every 24-hr. Upon cooling to room temperature, the solvent was removed and the residue was taken in methylene chloride. The solution was washed with water, brine and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 1-6% methanol in methylene chloride yielded 2-(2-benzyloxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazole (16.3 mg, 44%). HR-MS (ES, m/z) calculated for C28H23N2OCl2 [(M+H)+] 473.1185, observed 473.1183.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat gentle reflux for 54 h
  3. customthe solvent was removed
  4. washThe solution was washed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe solid was then filtered off
  7. concentrationthe filtrate was concentrated in vacuo
  8. customPurification of the crude residue by flash chromatography (Biotage, KP-Sil™ 32-63 μm, 60 Å silica gel)
  9. washeluting with 1-6% methanol in methylene chloride

Sources & evidence

ORD record
ord-c59dcd8e258644bd86c7c18149e1b921
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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