Water → 4-isopropyl-5-iodo-1H-imidazole

HRID 1415983Notes

Reaction equation

HRID 1415983 reaction equation
I[C:2]1[NH:3][C:4]([I:10])=[C:5]([CH:7]([CH3:9])[CH3:8])[N:6]=1.O.S([O-])([O-])=O.[Na+].[Na+]>C(O)C>[CH:7]([C:5]1[N:6]=[CH:2][NH:3][C:4]=1[I:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 24437Sodium SulfiteHCID 178440165HCID 178440165, compound

Product 1

HCID 1784401974-isopropyl-5-iodo-1H-imidazoleYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

In 240 ml of ethanol was dissolved 48.1 g (0.144 mol)of 2,5-diiodo-4-isopropyl-1H-imidazole (7), followed by addition of 240 ml of water and 20.1 g (0.159 mol)of sodium sulfite. The mixture was heated at 85° C. for 35 minutes. This reaction mixture was concentrated and extracted with methylene chloride and the extract was washed with water and dried over sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was washed with ethyl acetate-diisopropyl ether and filtered to provide 26.9 g (yield 86%)of 4-isopropyl-5-iodo-1H-imidazole (4b).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. extractionextracted with methylene chloride
  3. washthe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. washthe residue was washed with ethyl acetate-diisopropyl ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-081faacc0ad54bac935b09282f7b9505
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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