N-(2,3-Epoxypropyl)phthalimide → 2-[3-[3-(Dimethylaminomethyl)phenoxy]-2-hydroxy-propyl]-1H-isoindole-1,3-(2H)-dione

HRID 1589538

Reaktionsgleichung

Reaktionsgleichung von HRID 1589538
[O:1]1[CH2:3][CH:2]1[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].[CH3:16][N:17]([CH2:19][C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1)[CH3:18].[H-].[Na+]>CN(C)C=O.C(Cl)(Cl)Cl>[CH3:18][N:17]([CH2:19][C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[O:26][CH2:3][CH:2]([OH:1])[CH2:4][N:5]1[C:6](=[O:15])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]1=[O:14])[CH3:16]

Komponenten

6

Edukt 3

HCID 21601N-(2,3-Epoxypropyl)phthalimideHCID 24758Sodium hydrideHCID 328963-(Dimethylaminomethyl)phenol

Produkt 1

HCID 202460012-[3-[3-(Dimethylaminomethyl)phenoxy]-2-hydroxy-propyl]-1H-isoindole-1,3-(2H)-dioneAusbeute 39,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-(oxiranylmethyl)-1H-isoindole-1,3-(2H)-dione (20.3 g) and 3-(dimethylaminomethyl)phenol (22.3 g) in dimethylformamide (200 ml) with a catalytic amount of sodium hydride (0.2 g) was heated for 6 h at 100° under N2. The solvent was evaporated to give an oil which was dissolved in chloroform and washed with 2N sodium hydroxide and water. The organic solution was evaporated to give an oil (14 g). A portion of the oil (0.8 g) was distilled to give the title compound (0.6 g) as an oil, b.p. 250° (0.08 mmHg).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customto give an oil which
  3. washwashed with 2N sodium hydroxide and water
  4. customThe organic solution was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b92ba891a9cb4d749161f7465c9c11dd
Quelldatensatz
uspto-grants-1986_02
Patentnummer
US04571394

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