2-Chloroacetophenone → 2-phthalimido-acetophenone

HRID 1256237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256237
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K].[OH-].[Na+]>CN(C=O)C.C(Cl)Cl>[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][N:15]1[C:11](=[O:21])[C:12]2[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:14]1=[O:16]

Komponenten

6

Edukt 3

HCID 107572-ChloroacetophenoneHCID 14798Sodium HydroxideHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 2430382-phthalimido-acetophenoneAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 250 ml round-bottomed flask equipped with a magnetic stirrer is charged with 30 g of 2-chloroacetophenone and 36.3 g of potassium phthalimide in 120 ml of DMF. After 4 h at RT, the mixture is concentrated under vacuum. The solid obtained is taken up in 120 ml of DCM and 100 ml of 1 sodium hydroxide solution. The organic phase is washed with saturated aqueous NaCl solution, dried over MgSO4, filtered and concentrated under vacuum. The solid obtained is triturated in diisopropyl ether. The insolubles are filtered off and dried under vacuum to give 42.6 g of 2-(2-oxo-2-phenylethyl)-1H-isoindole-1,3(2H)-dione in the form of a beige solid, which is used as it is in the following step.

Aufarbeitung

  1. customA 250 ml round-bottomed flask equipped with a magnetic stirrer
  2. concentrationthe mixture is concentrated under vacuum
  3. customThe solid obtained
  4. washThe organic phase is washed with saturated aqueous NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe solid obtained
  9. customis triturated in diisopropyl ether
  10. filtrationThe insolubles are filtered off
  11. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4bc3d116565f4009b5804525b26c3071
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461175B2

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