N-(hydroxymethyl)phthalimide → Phthalamide

HRID 843708

Reaktionsgleichung

Reaktionsgleichung von HRID 843708
CC1C2C(=O)OC(=O)[NH:11]C=2C=CC=1.OC[N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26]>CS(O)(=O)=O.CCOCC>[C:17]([NH2:11])(=[O:26])[C:18]1[C:19](=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:20]([NH2:16])=[O:21]

Komponenten

5

Edukt 2

HCID 8354N-(hydroxymethyl)phthalimideHCID 104875225-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Produkt 1

HCID 6956PhthalamideAusbeute 168,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6395Methanesulfonic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 5-methyl-4H-3,1-benzoxazin-2,4-dione (Preparation VIIA) (19.7 g, 111 mmol) in methanesulfonic acid (150 mL) was added N-(hydroxymethyl)phthalimide (20.3 g, 111 mmol). The reaction mixture was heated to 50° C. and stirred for 3 hours. After cooling to room temperature, the reaction mixture was diluted with 2000 mL of Et2O. After stirring for an additional 1 hour, the precipitate was filtered, washed with Et2O and dried affording 30.7 g of crude phthalamide. 1H NMR showed a 3:2 mixture of the 6- and 8-substituted regioisomers respectively. The crude material was used directly in the next reaction where the two regeoisomers were separated.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. stirringAfter stirring for an additional 1 hour
  3. filtrationthe precipitate was filtered
  4. washwashed with Et2O
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b24de7fa85a843819bcf06fc5284d1fb
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06380189B1

Verknüpfte Notizen

Wird geladen…