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

HRID 4198

Reaktionsgleichung

Reaktionsgleichung von HRID 4198
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 3030034N-(2-(Phenylsulfonyl)ethyl)phthalimideAusbeute 35,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-6acd335397af4423ab4dfd5c48ff189b
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04724235

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