Dimethylformamide → HCID 14231038, compound

HRID 1607766Notes

Reaction equation

HRID 1607766 reaction equation
[F:1][CH2:2][C:3]([N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])([CH2:6][CH2:7][CH2:8][CH2:9]I)[C:4]#[N:5].CN(C=O)C.[C:27]1(=[O:37])[NH:31][C:30](=[O:32])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12.[K]>CC(C)=O>[F:1][CH2:2][C:3]([N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])([CH2:6][CH2:7][CH2:8][CH2:9][N:31]1[C:30](=[O:32])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]2[C:27]1=[O:37])[C:4]#[N:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 14579490HCID 14579490, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 14231038HCID 14231038, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-fluoromethyl-2-phthalimido-6-iodohexanenitrile (9.0 g, 22.5 mmol), dry DMF (30 ml), and potassium phthalimide (4.2 g, 1 equivalent) is stirred and heated at 80° C. for 4 hours. The DMF is removed under reduced pressure (0.1 mm Hg), and the residue is taken up in chloroform. The chloroform mixture is filtered and the filtrate is washed with 2N NaOH, 2N HCl, and water. Evaporation of solvent gives a residue which, when dissolved in the minimum amount of acetone, crystallizes upon addition of ether. After standing at 5° C. overnight, the colourless crystals of 2-fluoromethyl-2,6-diphthalimidohexanenitrile are collected (7.0 g), m.p. (Kofler) 136° C.

Workup

  1. customThe DMF is removed under reduced pressure (0.1 mm Hg)
  2. filtrationThe chloroform mixture is filtered
  3. washthe filtrate is washed with 2N NaOH, 2N HCl, and water
  4. customEvaporation of solvent
  5. customgives a residue which, when
  6. customcrystallizes upon addition of ether
  7. customthe colourless crystals of 2-fluoromethyl-2,6-diphthalimidohexanenitrile are collected (7.0 g), m.p. (Kofler) 136° C.

Sources & evidence

ORD record
ord-76130c3f73ef43f19524f75aa5c6a4eb
Source dataset
uspto-grants-1989_09
Patent number
US04866206

Reaction notes

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