((2-Chloroethyl)sulphonyl)benzene → N-(2-(Phenylsulfonyl)ethyl)phthalimide

HRID 745165Notes

Reaction equation

HRID 745165 reaction equation
Cl[CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[K]>CN(C)C=O>[C:7]1([S:4]([CH2:3][CH2:2][N:17]2[C:13](=[O:23])[C:14]3[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:16]2=[O:18])(=[O:6])=[O:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 13646((2-Chloroethyl)sulphonyl)benzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 3030034N-(2-(Phenylsulfonyl)ethyl)phthalimideYield 35.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 30.7 g (0.15 mole) of 2-chloroethylphenylsulfone and 69.5 g (0.375 mole) of potassium phthalimide in 600 ml of dimethylformamide was heated overnight at 85° C. The reaction mixture was stripped to dryness and the residue was partitioned between water and chloroform. The chloroform layer was dried and filtered and solvent was evaporated from the filtrate to give an oil which crystallized on standing. The solid was triturated with isopropyl ether and the mixture cooled under refrigeration. The solid was collected by filtration and dried and recrystallized from methanol-isopropyl ether to give white crystalline product, m.p. 186°-188° C., in 35.7% yield.

Workup

  1. customthe residue was partitioned between water and chloroform
  2. dry with materialThe chloroform layer was dried
  3. filtrationfiltered
  4. customsolvent was evaporated from the filtrate
  5. customto give an oil which
  6. customcrystallized
  7. customThe solid was triturated with isopropyl ether
  8. temperaturethe mixture cooled under refrigeration
  9. filtrationThe solid was collected by filtration
  10. customdried
  11. customrecrystallized from methanol-isopropyl ether
  12. customto give white crystalline product, m.p. 186°-188° C.

Sources & evidence

ORD record
ord-1fd35fa3094846588ab16ce17c632bbc
Source dataset
uspto-grants-1986_07
Patent number
US04597902

Reaction notes

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