N-3-Bromopropylphthalimide → N-[3-(2-phenylimidazol-1-yl)propyl]phthalimide

HRID 1078408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1078408
[C:1]1([C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:15][CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28]>CN(C=O)C>[C:1]1([C:7]2[N:11]([CH2:15][CH2:16][CH2:17][N:18]3[C:22](=[O:23])[C:21]4=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]4[C:19]3=[O:28])[CH:10]=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 695912-Phenylimidazole

Produkt 1

HCID 19429428N-[3-(2-phenylimidazol-1-yl)propyl]phthalimide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 2-phenylimidazole (14.4 g) in dry DMF (25 ml) was added dropwise to a stirred suspension of sodium hydride (4.0 g, 60% dispersion in oil) in dry DMF (125 ml) at ambient temperature under nitrogen for 2 hours. A slurry of N-(3-bromopropyl)phthalimide (25.5 g) in dry DMF (40 ml) was added and the mixture heated at 100° C. for 16 hours. The solvent was evaporated off and the residue was extracted with hot toluene. The combined toluene extracts were evaporated to dryness and the residue triturated with ether and dried to give N-[3-(2-phenylimidazol-1-yl)propyl]phthalimide, m.p. 109°-110.5° C.

Aufarbeitung

  1. customThe solvent was evaporated off
  2. extractionthe residue was extracted with hot toluene
  3. customThe combined toluene extracts were evaporated to dryness
  4. customthe residue triturated with ether
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c5807d56ecbd45a1af0a492341dacea5
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05547972

Notizen zur Reaktion

Wird geladen…