Potassium Carbonate → 2-butyl-4-chloro-1-(4-iodobenzyl)-1H-imidazole-5-carboxaldehyde

HRID 1779449Notes

Reaction equation

HRID 1779449 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[I:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>CN(C)C=O>[CH2:1]([C:5]1[N:6]([CH2:24][C:23]2[CH:26]=[CH:27][C:20]([I:19])=[CH:21][CH:22]=2)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 9542584-Iodobenzyl bromideHCID 178418251HCID 178418251, compound

Product 1

HCID 199555952-butyl-4-chloro-1-(4-iodobenzyl)-1H-imidazole-5-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-butyl-4-chloro-1H-imidazole-5-carboxaldehyde (4.0 g; preparable as described in Drugs of the Future (1991), Vol. 16, p 305), potassium carbonate (2.94 g) and dry dimethylformamide (50 ml) was stirred for 15 minutes at ambient temperature. 4-Iodobenzyl bromide (6.34 g) was added to the resulting mixture and stirring was continued for approximately 17 hours. The solvent was then evaporated under reduced pressure at 80° C. Water (200 ml) was added to the resulting residue which was then extracted with diethyl ether (2×100 ml). The combined extracts were washed with water (50 ml) and dried over magnesium sulphate. The solvent was evaporated. The resulting residue was purified by flash chromatography on silica gel (eluting with dichloromethane/methanol (80:1)) to give the intermediate compound 2-butyl-4-chloro-1-(4-iodobenzyl)-1H-imidazole-5-carboxaldehyde as an oil (6.9 g).

Workup

  1. stirringstirring
  2. waitwas continued for approximately 17 hours
  3. customThe solvent was then evaporated under reduced pressure at 80° C
  4. additionWater (200 ml) was added to the resulting residue which
  5. extractionwas then extracted with diethyl ether (2×100 ml)
  6. washThe combined extracts were washed with water (50 ml)
  7. dry with materialdried over magnesium sulphate
  8. customThe solvent was evaporated
  9. customThe resulting residue was purified by flash chromatography on silica gel (eluting with dichloromethane/methanol (80:1))

Sources & evidence

ORD record
ord-dfdd619e5a1641f0a9ec9c88fb95ae71
Source dataset
uspto-grants-1997_05
Patent number
US05627191

Reaction notes

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