Potassium Iodide → 2-[6-(Pyrimidin-5-yl)hexyl]-1H-isoindole-1,3(2H)-dione

HRID 1583414Notes

Reaction equation

HRID 1583414 reaction equation
[N:1]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]Cl)[CH:4]=[N:3][CH:2]=1.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K].[I-].[K+]>CN(C)C=O.O>[N:1]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:18]2[C:14](=[O:24])[C:15]3[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:17]2=[O:19])[CH:4]=[N:3][CH:2]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 139997535-(6-Chlorohexyl)pyrimidineHCID 24194345Phthalimide potassium salt

Product 1

HCID 135575542-[6-(Pyrimidin-5-yl)hexyl]-1H-isoindole-1,3(2H)-dioneYield 71.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 22.3 g of 6-(5-pyrimidinyl)hexyl chloride, 41.6 g of potassium phthalimide, and 1.8 g of potassium iodide in 180 ml of dimethylformamide was heated to a bath temperature of 130° C. for 1 hour. The mixture was diluted with water and was extracted with dichloromethane. The combined organic layers were washed with water and were dried over potassium carbonate. The residue obtained after evaporation was crystallized from ethyl acetate-hexane to give 24.7 g (71%) of 2-[6-(5-pyrimidinyl)hexyl]-1H-isoindole-1,3-(2H)-dione, mp 124°-126.5° C.

Workup

  1. extractionwas extracted with dichloromethane
  2. washThe combined organic layers were washed with water
  3. dry with materialwere dried over potassium carbonate
  4. customThe residue obtained
  5. customafter evaporation
  6. customwas crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-55b7fa63147e4b249768d30f77e04cb2
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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