Sodium Iodide → 2-Fluoromethyl-2-phthalimido-5-iodopentanenitrile

HRID 1252570Notes

Reaction equation

HRID 1252570 reaction equation
[F:1][CH2:2][C:3]([N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])([CH2:6][CH2:7][CH2:8]OS(C)(=O)=O)[C:4]#[N:5].[I-:25].[Na+]>CC(C)=O.CCOCC>[F:1][CH2:2][C:3]([N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])([CH2:6][CH2:7][CH2:8][I:25])[C:4]#[N:5]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 198510892-Fluoromethyl-2-phthalimido-5-methanesulfonyloxypentanenitrile

Product 1

HCID 147716572-Fluoromethyl-2-phthalimido-5-iodopentanenitrile

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-fluoromethyl-2-phthalimido-5-methanesulfonyloxypentanenitrile (42 g) and sodium iodide (35.7 g) in acetone (600 ml) is stirred and heated under reflux. After about 1/2 hour, the mixture solidifies. Acetone (500 ml) is added, and refluxing and stirring is continued overnight. The salts are removed by filtration and washed several times with acetone. The acetone is evaporated to give a residue which is dissolved in ether (1.5 l). The ether solution is washed subsequently with water (2×), sodium sulfite solution, and water again (3×). After drying (MgSO4) and evaporating the ether, 2-fluoromethyl-2-phthalimido-5-iodopentanenitrile is obtained as an oil (34.1 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. temperaturerefluxing
  4. waitis continued overnight
  5. customThe salts are removed by filtration
  6. washwashed several times with acetone
  7. customThe acetone is evaporated
  8. customto give a residue which
  9. washThe ether solution is washed subsequently with water (2×), sodium sulfite solution, and water again (3×)
  10. dry with materialAfter drying (MgSO4)
  11. customevaporating the ether

Sources & evidence

ORD record
ord-07bd525284ed4723919df780a048571e
Source dataset
uspto-grants-1988_05
Patent number
US04743691

Reaction notes

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