1-Chloro-4-[(3-chloropropyl)sulfonyl]benzene → 2-[3-[(4-Chlorophenyl)sulfonyl]propyl]-1,3-dihydro-2H-isoindole-1,3-dione

HRID 4189Notes

Reaction equation

HRID 4189 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.[K]>CN(C)C=O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([S:5]([CH2:4][CH2:3][CH2:2][N:19]2[C:15](=[O:25])[C:16]3[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:18]2=[O:20])(=[O:7])=[O:6])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 167842621-Chloro-4-[(3-chloropropyl)sulfonyl]benzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 136551572-[3-[(4-Chlorophenyl)sulfonyl]propyl]-1,3-dihydro-2H-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 17.8 g (0.07 mole) of 1-chloro-3-(p-chlorophenylsulfonyl)propane and 15.2 g (0.082 mole) of potassium phthalimide in 300 ml of dimethylformamide was stirred at 90°-110° C. for 2 hr and then quenched in water. The mixture was extracted with methylene chloride and the methylene chloride layer dried over magnesium sulfate. Diethylether and hexane were added and the solution stored at 0° C. overnight. The crystalline product was recrystallized from methylene chloride diethyl ether to give a white crystalline product, m.p. 187.5°-188.5° C.

Workup

  1. customquenched in water
  2. extractionThe mixture was extracted with methylene chloride
  3. dry with materialthe methylene chloride layer dried over magnesium sulfate
  4. additionDiethylether and hexane were added
  5. customThe crystalline product was recrystallized from methylene chloride diethyl ether
  6. customto give a white crystalline product, m.p. 187.5°-188.5° C.

Sources & evidence

ORD record
ord-a8eb42d4c700427bb2f6aedd4d4b659d
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Reaction notes

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