Dimethylformamide → 3-(4-Bromobenzyl)-5-chloro-2-phenyl-3H-imidazole-4-carbaldehyde

HRID 2301960Notes

Reaction equation

HRID 2301960 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:6]=1[CH:7]=[O:8].C([O-])([O-])=O.[K+].[K+].CN(C=O)C.[Br:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1>CC(=O)OCC>[Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:5]([CH2:31][C:30]2[CH:33]=[CH:34][C:27]([Br:26])=[CH:28][CH:29]=2)[C:6]=1[CH:7]=[O:8]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 178520008HCID 178520008, compound

Product 1

HCID 109157723-(4-Bromobenzyl)-5-chloro-2-phenyl-3H-imidazole-4-carbaldehydeYield 95.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 8.0 g (32.0 mmol) of 4-chloro-5-formyl-2-phenylimidazole (prepared according to Chem. Pharm. Bull. 24 (1976) 960-969) and 5.3 g (32.0 mmol) of K2CO3 in 200 ml of abs. DMF was stirred at RT for 20 min. A solution of 9.6 g (32.0 mmol) of 4-bromobenzyl bromide in 200 ml of abs. DMF was then added dropwise and the reaction solution was stirred at RT for 6 h. It was concentrated in vacuo, and the residue obtained was taken up in EA, washed with water, 10% strength KHSO4, 10% strength NaHCO3, and satd sodium chloride solution, and dried over Na2SO4. Chromatographic purification on SiO2 using EA/heptane (1:4) as eluent of the residue which remained after stripping off the EA yielded 11.5 g of the title compound in the form of a beige solid.

Workup

  1. concentrationIt was concentrated in vacuo
  2. customthe residue obtained
  3. washwashed with water, 10% strength KHSO4, 10% strength NaHCO3, and satd sodium chloride solution
  4. dry with materialdried over Na2SO4
  5. customChromatographic purification on SiO2

Sources & evidence

ORD record
ord-6be633c7f0e045a7913c03571c94cd70
Source dataset
uspto-grants-2002_08
Patent number
US06429222B2

Reaction notes

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