Sodium Iodide → HCID 69799308, compound

HRID 2179938Notes

Reaction equation

HRID 2179938 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][CH2:13]Cl)[CH:3]=1.[I-:21].[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][CH2:13][I:21])[CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 20779195HCID 20779195, compound

Product 1

HCID 69799308HCID 69799308, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Chloro-2-{[(1R)-3-chloro-1-phenylpropyl]oxy}benzonitrile (220mg, 0.718 mmol) was dissolved in acetone (20 ml) which had previously been saturated with sodium iodide and the solution was heated under reflux for 18 h. The reaction mixture was cooled, filtered, evaporated and the residue partitioned between water and ethyl acetate. The organic layer was separated, washed twice with water and dried (magnesium sulphate). The solvent was evaporated to leave 0.24 g (84%) of the product as a yellow oil. This was used without purification for the next step.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 18 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customevaporated
  6. customthe residue partitioned between water and ethyl acetate
  7. customThe organic layer was separated
  8. washwashed twice with water
  9. dry with materialdried (magnesium sulphate)
  10. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ec757257be6f47069bdcb43ee8ad3701
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

Loading…