Sodium Iodide → HCID 20435938, compound

HRID 1154037Notes

Reaction equation

HRID 1154037 reaction equation
CS(O[CH2:6][CH2:7][C:8]1([CH3:23])[C:20](=[O:21])[N:11]2[CH2:12][CH:13]=[CH:14][CH:15]([C:16]([O:18][CH3:19])=[O:17])[N:10]2[C:9]1=[O:22])(=O)=O.[I-:24].[Na+]>CC(C)=O>[I:24][CH2:6][CH2:7][C:8]1([CH3:23])[C:20](=[O:21])[N:11]2[CH2:12][CH:13]=[CH:14][CH:15]([C:16]([O:18][CH3:19])=[O:17])[N:10]2[C:9]1=[O:22]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 20435967HCID 20435967, compound

Product 1

HCID 20435938HCID 20435938, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7.6 g (22 mmol) of methyl 2,3,5,8-tetrahydro-2-(2-methanesulfonyloxyethyl)-2-methyl-1,3-dioxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylate and 6.6 g (44 mmol) of sodium iodide in 100 ml of acetone was heated under reflux for 16 hours. The resulting suspension was filtered and the filtrate was evaporated to dryness. The residue was partitioned between dichloromethane and water. The organic solution was washed with 10% aqueous sodium thiosulfate, dried over magnesium sulfate and evaporated to give 6.7 g (80%) of methyl 2,3,5,8-tetrahydro-2-(2-iodoethyl)-2-methyl-1,3-dioxo-1H-pyrazolo[1,2-a]-pyridazine-5-carboxylate having a melting point of 86°-87° C. (from diethyl ether).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. filtrationThe resulting suspension was filtered
  4. customthe filtrate was evaporated to dryness
  5. customThe residue was partitioned between dichloromethane and water
  6. washThe organic solution was washed with 10% aqueous sodium thiosulfate
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-6bdb3861728946d3be8fad82ffb50c1f
Source dataset
uspto-grants-1984_12
Patent number
US04487929

Reaction notes

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