Sodium Iodide → 2-(3-Iodo-propyl)-isoindole-1,3-dione

HRID 1858334Notes

Reaction equation

HRID 1858334 reaction equation
[I-:1].[Na+].Br[CH2:4][CH2:5][CH2:6][N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17]>CC(C)=O>[I:1][CH2:4][CH2:5][CH2:6][N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 21611N-3-Bromopropylphthalimide

Product 1

HCID 2302832-(3-Iodo-propyl)-isoindole-1,3-dioneYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 15 g (100 mmol) of sodium iodide in 120 ml of acetone was added 3 g (11 mmol) of N-(3-bromopropyl)phthalimide and the mixture was heated at reflux for 30 minutes. The cooled mixture was filtered and evaporated. The residue was partitioned between 50 ml of diethyl ether and 50 ml of water. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 2.6 g (75%) of N-(3-iodopropyl)phthalimide as a white solid. [Mass spectrum (ESI) MH+ =316].

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. filtrationThe cooled mixture was filtered
  4. customevaporated
  5. customThe residue was partitioned between 50 ml of diethyl ether and 50 ml of water
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-56f9d958bc064da99a8f23292a13192c
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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