Pyridine → 1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl benzoate

HRID 1241252

Reaktionsgleichung

Reaktionsgleichung von HRID 1241252
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].N1C=CC=CC=1.O1CCOCC1.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O>[C:25]([O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 10665N-HydroxyphthalimideHCID 312751,4-Dioxane

Produkt 1

HCID 7925791,3-dioxo-2,3-dihydro-1H-isoindol-2-yl benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

In a 3-L flask equipped with a stirrer and thermometer, 100 g (613 mmol) of N-hydroxyphthalimide, 53.3 g (674 mmol) of pyridine and 1100 g of 1,4-dioxane were placed and were stirred at room temperature. To the resulting mixture 94.8 g (674 mmol) of benzoyl chloride was added dropwise over 1 hour, and the resulting mixture was stirred at room temperature for further 2 hours. Subsequently, 1100 g of pure water was added dropwise over 30 minutes to dissolve by-produced salts and thereby yielded a crystal of the target N-benzoyloxyphthalimide. The mixture was stirred and aged for further 1 hour, the crystal was filtrated using a Nutsche, was rinsed with an appropriate amount of water, was dried at 60° C. under a reduced pressure and thereby yielded 162 g (604 mmol) of N-benzoyloxyphthalimide in a yield of 98.6% on the basis of N-hydroxyphthalimide.

Aufarbeitung

  1. customIn a 3-L flask equipped with a stirrer
  2. stirringthe resulting mixture was stirred at room temperature for further 2 hours
  3. dissolutionto dissolve
  4. customby-produced salts

Quellen und Nachweise

ORD-Eintrag
ord-540120541a7f428a95c9c5e4a4d6067e
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115541B2

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