Sodium Iodide → HCID 131716716, compound

HRID 892524Notes

Reaction equation

HRID 892524 reaction equation
CS(O)(=O)=O.CS(O[CH:11]([C:20]([CH3:30])([S:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1)[CH3:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N+:14]=1[O-:19])(=O)=O.[I-:31].[Na+]>CC(C)=O>[I:31][CH:11]([C:20]([CH3:30])([S:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1)[CH3:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N+:14]=1[O-:19]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 131716713HCID 131716713, compound

Product 1

HCID 131716716HCID 131716716, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3.35 g of 2-[2-methanesulphonyloxy-3-methyl-3-(4-methylthiophenoxy)butyl]pyridine N-oxide methanesulphonic acid salt and 2.25 g of sodium iodide in 50 ml of acetone was heated under reflux for 2 hours. The mixture was filtered and the filtrate was evaporated. The residue was partitioned between water and dichloromethane and the organic phase was evaporated. The residue was taken up in 50 ml of acetone and heated under reflux for 2 hours with 2.25 g of sodium iodide. The cooled reaction mixture was then evaporated and the residue was partitioned between water and dichloromethane. The organic phase was evaporated and the residue was crystallized from dichloromethane/ethyl acetate to give 1.8 g of 2-[2-iodo-3-methyl-3-(4-methylthiophenoxy)butyl]pyridine N-oxide in the form of a pale yellow solid of melting point 191°-193° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was partitioned between water and dichloromethane
  5. customthe organic phase was evaporated
  6. temperatureheated
  7. temperatureunder reflux for 2 hours with 2.25 g of sodium iodide
  8. customThe cooled reaction mixture
  9. customwas then evaporated
  10. customthe residue was partitioned between water and dichloromethane
  11. customThe organic phase was evaporated
  12. customthe residue was crystallized from dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-08017c87bf0642c0a79a618b4ddb8c56
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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