Iodine → HCID 178491398, compound

HRID 1415994Notes

Reaction equation

HRID 1415994 reaction equation
C(Cl)Cl.[CH:4]([C:7]1[N:8]=[C:9]([CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[NH:10][CH:11]=1)([CH3:6])[CH3:5].[I:23]I.[OH-].[Na+]>O.CO>[I:23][C:11]1[NH:10][C:9]([CH2:12][O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[N:8][C:7]=1[CH:4]([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 807IodineHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 178491399HCID 178491399, compound

Product 1

HCID 178491398HCID 178491398, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(3)In methylene chloride (60 ml)-methanol (660 ml) 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 magnesium sulfate. The solvent was then distilled off under reduced pressure and 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 magnesium sulfate
  8. distillationThe solvent was then distilled off under reduced pressure
  9. washthe residue was rinsed with isopropyl ether
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-71d6d43b79ad4a07b238e64cb8b489cc
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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