Water → 2-(2-(2,5-Dichlorophenyl)-2-oxoethyl)isoindoline-1,3-dione

HRID 474341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 474341
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[Cl:12])=[O:4].[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].O>CN(C)C=O>[Cl:12][C:6]1[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:5]=1[C:3](=[O:4])[CH2:2][N:17]1[C:13](=[O:23])[C:14]2[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16]1=[O:18]

Komponenten

5

Edukt 3

HCID 962WaterHCID 27569072-Bromo-1-(2,5-dichlorophenyl)ethanoneHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 580633722-(2-(2,5-Dichlorophenyl)-2-oxoethyl)isoindoline-1,3-dioneAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To an ice-cooled solution of 2-bromo-1-(2,5-dichlorophenyl)ethanone (0.10 g, 0.37 mmol) in N,N-dimethylformamide (8 mL) was added potassium phthalimide (76 mg, 0.41 mmol). The mixture was warmed to room temperature for 2 hours. The resultant mixture was then poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. Recrystallization with diethyl ether afforded 2-(2-(2,5-dichlorophenyl)-2-oxoethyl)isoindoline-1,3-dione as a white solid. (110 mg, 88% yield). 1H NMR (400 MHz, CDCl3): 7.92-7.94 (m, 2H), 7.78-7.80 (m, 2H), 7.72 (m, 1H), 7.45-7.46 (m, 2H), 5.08 (s, 2H).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customRecrystallization with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-20b22d45a9e8430c9f559094decc2ce3
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637526B2

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