Dimethylformamide → HCID 14231038, compound

HRID 1995575Notes

Reaction equation

HRID 1995575 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-iodo-hexanenitrile (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 2 N NaOH, 2 N 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 are collected (7.0 g), mp (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 2 N NaOH, 2 N HCl, and water
  4. customEvaporation of solvent
  5. customgives a residue which, when
  6. customcrystallizes upon addition of ether
  7. customthe colourless crystals are collected (7.0 g), mp (Kofler) 136° C.

Sources & evidence

ORD record
ord-f6e87f7d33a04f77ba3149d4750ec3ca
Source dataset
uspto-grants-1983_09
Patent number
US04405530

Reaction notes

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