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

HRID 1995558Notes

Reaction equation

HRID 1995558 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)C=O>[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-diphthalimidopentanenitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoromethyl-2-phthalimido-5-iodo-valeronitrile (1.20 g, 3.11 mmol) and potassium phthalimide (0.75 g, 4 mmol) are heated in dimethylformamide (25 ml) to 80° C. for 2 hours. After standing overnight at room temperature, the DMF is removed by vacuum distillation and the residue is dissolved in chloroform and washed with 1 N KOH and water. After drying (Na2SO4), evaporation gives 2-fluoromethyl-2,5-diphthalimidovaleronitrile as a solid.

Workup

  1. customthe DMF is removed by vacuum distillation
  2. dissolutionthe residue is dissolved in chloroform
  3. washwashed with 1 N KOH and water
  4. customAfter drying
  5. custom(Na2SO4), evaporation

Sources & evidence

ORD record
ord-4b736076ed8e46dc97c516069188dce1
Source dataset
uspto-grants-1983_09
Patent number
US04405530

Reaction notes

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