Carbon Dioxide → HCID 178440069, compound

HRID 1857770Notes

Reaction equation

HRID 1857770 reaction equation
[OH-].[Na+].O.[CH2:4]([O:11][CH2:12][CH2:13][CH2:14][C:15]1[NH:16][CH:17]=[C:18]([CH:20]([CH3:22])[CH3:21])[N:19]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[I:23]I.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)=O>O1CCOCC1.O>[CH2:4]([O:11][CH2:12][CH2:13][CH2:14][C:15]1[NH:16][C:17]([I:23])=[C:18]([CH:20]([CH3:22])[CH3:21])[N:19]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 807IodineHCID 24477Sodium ThiosulfateHCID 23719242Sodium hydroxide--water (1/1/1)HCID 178439622HCID 178439622, compound

Product 1

HCID 178440069HCID 178440069, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A four-necked flask of one-liter capacity was charged with 25 g of 40% sodium hydroxide/H2O and 125 ml of water, followed by addition of a solution of the imidazole (135a) obtained above in dioxane (125 ml). Then, 70.5 g (278 mmol) of solid iodine was added under ice-cooling and the mixture was stirred. After 1 hour, an aqueous solution of sodium thiosulfate and, then, dry-ice were added and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in diethyl ether and 39 g of oxalic acid was added to the solution. The precipitated crystals was collected by filtration, neutralized with sodium carbonate, and extracted with chloroform. The extract was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 86.7 g (yield 82%) of 2-(3-benzyloxypropyl)-5-iodo-4-isopropyl-1H-imidazole (135b) as oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in diethyl ether
  7. addition39 g of oxalic acid was added to the solution
  8. filtrationThe precipitated crystals was collected by filtration
  9. extractionextracted with chloroform
  10. washThe extract was washed with water
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e7fab5fc8a6c4489888b18f56ea1c205
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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