Water → 2-(1-Methylethoxy)-1H-isoindole-1,3(2H)-dione

HRID 600951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600951
C(=O)([O-])[O-].[K+].[K+].[OH:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].[CH:19](Br)([CH3:21])[CH3:20].O>CS(C)=O>[CH:19]([O:7][N:8]1[C:9](=[O:18])[C:10]2[C:11](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:13])([CH3:21])[CH3:20]

Komponenten

6

Edukt 4

HCID 962WaterHCID 63582-BromopropaneHCID 10665N-HydroxyphthalimideHCID 11430Potassium Carbonate

Produkt 1

HCID 27689132-(1-Methylethoxy)-1H-isoindole-1,3(2H)-dioneAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Solid potassium carbonate (8.64 g, 62.5 mmol) was added to a solution of N-hydroxyphthalimide (4.08 g, 25.0 mmol) in dimethyl sulfoxide (37 mL), and the mixture was stirred at 25° C. for 5 min. To the mixture, isopropyl bromide (3.41 mL, 37.5 mmol) was added, and the mixture stirred at 80° C. for 3 h. After ice-cooling, the mixture was poured into cold water and the resulting precipitate was collected by filtration in vacuo, washed with water (25 mL) and hexanes (15 mL) and dried in vacuo to afford 2-isopropyloxy-isoindole-1,3-dione (4.44 g, 86.6%) as a white solid which was used in the next step without further purification.

Aufarbeitung

  1. stirringthe mixture stirred at 80° C. for 3 h
  2. temperatureAfter ice-cooling
  3. filtrationthe resulting precipitate was collected by filtration in vacuo
  4. washwashed with water (25 mL) and hexanes (15 mL)
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1a14b19a546e44f4939490745ee5b5fc
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902248B2

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