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

HRID 977299Notes

Reaction equation

HRID 977299 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 1N KOH and water. After drying (Na2SO4), evaporation gives 2-fluoromethyl-2,5-diphthalimido-valeronitrile as a solid.

Workup

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

Sources & evidence

ORD record
ord-967551eef0d04158a459b7d3dbdef65e
Source dataset
uspto-grants-1997_03
Patent number
US05614557

Reaction notes

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