Benzyl Bromide → HCID 86719608, compound

HRID 922617Notes

Reaction equation

HRID 922617 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].[CH2:10]([Br:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(#N)C>[Br-:17].[CH2:10]([N:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[N+:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7498Benzyl Bromide2×HCID 14797Potassium HydroxideHCID 1400184,5-Dichloroimidazole

Product 1

HCID 86719608HCID 86719608, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4,5-dichloroimidazole (1.00 g, 7.36 mmol) was dissolved in acetonitrile. Potassium hydroxide (0.828 g, 14.72 mmol) was added to the solution and allowed to reflux for 30 min. 1 equivalent of benzyl bromide (1.26 g, 7.36 mmol) was added to the solution and refluxed for 2.5 h. Solution was filtered hot to remove the KBr precipitate and placed back onto reflux. The second equivalent of benzyl bromide (1.38 g, 8.10 mmol) was added to solution and refluxed for 1.5 h. The solution was cooled and the white precipitate was collected and analyzed. Yield: 93%. 1H NMR (500 MHz, DMSO-d6): δ 5.55 (s, 4H, CH2), 7.43-7.46 (m, 10H, aryl), 9.86 (s, 1H, NCHN); 13C NMR (125 MHz, DMSO-d6): δ 51.50, 119.11, 128.27, 128.84, 128.93, 132.61, 136.68

Workup

  1. temperatureto reflux for 30 min
  2. temperaturerefluxed for 2.5 h
  3. filtrationSolution was filtered hot
  4. customto remove the KBr precipitate
  5. temperatureonto reflux
  6. temperaturerefluxed for 1.5 h
  7. temperatureThe solution was cooled
  8. customthe white precipitate was collected

Sources & evidence

ORD record
ord-ce562f1d9d534288a6e73bd651106f80
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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