Water → 4-Chloro-1-(2-chloro-4-iodobenzyl)-2-methylimidazole-5-carbaldehyde

HRID 1828811Notes

Reaction equation

HRID 1828811 reaction equation
[Cl:1][C:2]1[NH:6][C:5]([CH3:7])=[N:4][C:3]=1[CH:8]=[O:9].C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[CH:24]=[C:23]([I:25])[CH:22]=[CH:21][C:18]=1[CH2:19]Br.O>CN(C)C=O.[Cl-].[Na+].O>[Cl:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([CH2:19][C:18]2[CH:21]=[CH:22][C:23]([I:25])=[CH:24][C:17]=2[Cl:16])[C:3]=1[CH:8]=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 20061014HCID 20061014, compoundHCID 220586831-(Bromomethyl)-2-chloro-4-iodobenzene

Product 1

HCID 155242134-Chloro-1-(2-chloro-4-iodobenzyl)-2-methylimidazole-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 5-chloro-2-methylimidazole-4-carbaldehyde (433 mg) in N,N-dimethylformamide (4.3 ml) were added potassium carbonate powder (616 mg) and 2-chloro-4-iodobenzyl bromide (1.2 equivalents) under ice-cooling and the mixture was stirred at room temperature for 2.5 hr. To the reaction mixture were added water and saturated brine, and the resulting product was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give 4-chloro-1-(2-chloro-4-iodobenzyl)-2-methylimidazole-5-carbaldehyde (1.01 g) as a white powder.

Workup

  1. temperaturecooling
  2. extractionthe resulting product was extracted twice with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-d1c549416f19477283c7bc6406b9439c
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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