Sodium Iodide → HCID 14579490, compound

HRID 1607765Notes

Reaction equation

HRID 1607765 reaction equation
[F:1][CH2:2][C:3]([N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])([CH2:6][CH2:7][CH2:8][CH2:9]OS(C)(=O)=O)[C:4]#[N:5].[I-:26].[Na+]>CC(C)=O.CCOCC>[F:1][CH2:2][C:3]([N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])([CH2:6][CH2:7][CH2:8][CH2:9][I:26])[C:4]#[N:5]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 14579489HCID 14579489, compound

Product 1

HCID 14579490HCID 14579490, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

2-Fluoromethyl-2-phthalimido-6-methanesulfonyloxyhexanenitrile (10.84 g, 29.5 mmol) and sodium iodide (8.8 g, 2 equivalents) are refluxed in acetone overnight. The reaction mixture is filtered and solvent is removed by evaporation. The residue obtained is dissolved in ether and washed with water, sodium bisulfite, and water again. Upon concentration, 2-fluoromethyl-2-phthalimido-6-iodoheanenitrile crystallizes (9.0 g).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customsolvent is removed by evaporation
  3. customThe residue obtained
  4. washwashed with water, sodium bisulfite, and water again
  5. concentrationUpon concentration, 2-fluoromethyl-2-phthalimido-6-iodoheanenitrile
  6. customcrystallizes (9.0 g)

Sources & evidence

ORD record
ord-5ef45ba7a6724cb3a73f73c924fddacb
Source dataset
uspto-grants-1989_09
Patent number
US04866206

Reaction notes

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