2-Fluoromethyl-2-phthalimido-5-iodopentanenitrile → 2-Fluoromethyl-2,5-diphthalimidopentanenitrile

HRID 1995569Notes

Reaction equation

HRID 1995569 reaction equation
[F:1][CH2:2][C:3]([N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20])([CH2:6][CH2:7][CH2:8]I)[C:4]#[N:5].[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12.[K]>CN(C=O)C>[F:1][CH2:2][C:3]([N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20])([CH2:6][CH2:7][CH2:8][N:25]1[C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]2[C:21]1=[O:31])[C:4]#[N:5]

Participants

4

Reactant 2

HCID 147716572-Fluoromethyl-2-phthalimido-5-iodopentanenitrileHCID 24194345Phthalimide potassium salt

Product 1

HCID 199663332-Fluoromethyl-2,5-diphthalimidopentanenitrileYield 51.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-fluoromethyl-2-phthalimido-5-iodo-valeronitrile (34.1 g), potassium phthalimide (16.6 g), and dry DMF (230 ml) is stirred and heated at 70°-80° C. for 5 hours. The DMF is removed under reduced pressure, the residue is dissolved in chloroform, and the chloroform solution is washed with water (2×), 1 N KOH (2×), 1 N HCl, and water again (3×). The washed chloroform solution is dried and solvent removed to give an oil which is evaporated twice with chloroform/ether to give a solid. Recrystallization from ether (500 ml) gives the pure title compound (18.5 g).

Workup

  1. temperatureheated at 70°-80° C. for 5 hours
  2. customThe DMF is removed under reduced pressure
  3. dissolutionthe residue is dissolved in chloroform
  4. washthe chloroform solution is washed with water (2×), 1 N KOH (2×), 1 N HCl, and water again (3×)
  5. dry with materialThe washed chloroform solution is dried
  6. customsolvent removed
  7. customto give an oil which
  8. customis evaporated twice with chloroform/ether
  9. customto give a solid
  10. customRecrystallization from ether (500 ml)

Sources & evidence

ORD record
ord-353717da5bf045dd8172f68ed0e79b9d
Source dataset
uspto-grants-1983_09
Patent number
US04405530

Reaction notes

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