Potassium Carbonate → 2-(8-Bromooctyl)-4,5-diphenyltriazole

HRID 265405Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 265405
[C:1]1([C:7]2[N:8]=[N:9][NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:9]1[N:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[N:10]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 783101,8-DibromooctaneHCID 178420171HCID 178420171, Verbindung

Produkt 1

HCID 229163312-(8-Bromooctyl)-4,5-diphenyltriazoleAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 4,5-diphenyltriazole (11 g), 1,8-dibromooctane (67.6 g), and potassium carbonate (10.31 g) in dry butanone (300 ml) was heated at reflux temperature for 24 hours. The mixture was filtered and the solvent evaporated to give an oily residue. Distillation to remove 1,8-dibromooctane and column chromatography on silica gel eluted with a hexane:ethyl acetate gradient gave 2-(8-bromooctyl)-4,5-diphenyl-triazole (11.13 g, 54%) as an oil. NMR d (CDCl3) 1.2-1.5 (8H, m, 4×CH2), 1.84 (2H, m, CH2), 2.05 (2H, m, CH2), 3.37 (2H, t, Br--CH2), 4.47 (2H, t, N--CH2), 7.3-7.6 (10H, m, 2×Ph) ppm

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux temperature for 24 hours
  3. filtrationThe mixture was filtered
  4. customthe solvent evaporated
  5. customto give an oily residue
  6. distillationDistillation
  7. customto remove 1,8-dibromooctane and column chromatography on silica gel
  8. washeluted with a hexane

Quellen und Nachweise

ORD-Eintrag
ord-ce4e6f0c97dc437d96e53030c8cc822b
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648373

Notizen zur Reaktion

Wird geladen…