Iodine → HCID 178491398, compound

HRID 1857697Notes

Reaction equation

HRID 1857697 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[NH:7][CH:8]=1)([CH3:3])[CH3:2].[I:20]I.[OH-].[Na+]>C(Cl)Cl.CO.O>[I:20][C:8]1[NH:7][C:6]([CH2:9][O:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)=[N:5][C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 178491399HCID 178491399, compound

Product 1

HCID 178491398HCID 178491398, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (60 ml)-methanol (660 ml) was dissolved 165 g (0.67 mol) of 4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole (3d), followed by addition of 170 g of solid iodine. Then, an aqueous solution prepared by dissolving 27.3 g (0.67 mol) of sodium hydroxide in 85 ml of water was added dropwise under ice-cooling. After completion of dropwise addition, the reaction mixture was stirred at room temperature for 1.5 hours. This reaction mixture was extracted with methylene chloride and the organic layer was washed with an aqueous solution of sodium sulfite and dried over anhydrous magnisium sulfate. The solvent was then distilled off under reduced pressure arid the residue was rinsed with isopropyl ether and collected by filtration to provide 209.5 g (yield 81%) of 5-iodo-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole (4d). mp 78-79° C.

Workup

  1. customThen, an aqueous solution prepared
  2. additionwas added dropwise under ice-
  3. temperaturecooling
  4. additionAfter completion of dropwise addition
  5. extractionThis reaction mixture was extracted with methylene chloride
  6. washthe organic layer was washed with an aqueous solution of sodium sulfite
  7. dry with materialdried over anhydrous magnisium sulfate
  8. distillationThe solvent was then distilled off under reduced pressure
  9. washwas rinsed with isopropyl ether
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-fc68394615b4429191d5621768966001
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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