3-Chloropropyl phenyl sulfide → 2-(3-(phenylthio)propyl)-1H-isoindole-1,3(2H)-dione

HRID 4193Notes

Reaction equation

HRID 4193 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.[K]>CN(C)C=O>[C:6]1([S:5][CH2:4][CH2:3][CH2:2][N:16]2[C:12](=[O:22])[C:13]3[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:15]2=[O:17])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 2696063-Chloropropyl phenyl sulfideHCID 24194345Phthalimide potassium salt

Product 1

HCID 2651852-(3-(phenylthio)propyl)-1H-isoindole-1,3(2H)-dioneYield 63.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 32.86 g (0.177 mole) of 1-chloro-3-(phenylthio)propane and 33.7 g (0.182 mole) of potassium phthalimide in 500 ml of dimethylformamide was stirred at 80° C. for 19 hr. The dimethylformamide was removed in vacuo. The residue was dissolved in methylene chloride and the resulting solution extracted with several portions of dilute sodium hydroxide solution. The methylene chloride layer was dried over magnesium sulfate, filtered, and the filtrate evaporated in vacuo. The resulting solid residue was recrystallized from methylene chloride-hexane to give 33.56 g (63.8%) of white crystalline product, m.p. 83°-85° C.

Workup

  1. customThe dimethylformamide was removed in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride
  3. extractionthe resulting solution extracted with several portions of dilute sodium hydroxide solution
  4. dry with materialThe methylene chloride layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated in vacuo
  7. customThe resulting solid residue was recrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-ce8e45175ab64e68b2f9eff595f3864a
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Reaction notes

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