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

HRID 265405Notes

Reaction equation

HRID 265405 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 229163312-(8-Bromooctyl)-4,5-diphenyltriazoleYield 54.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-ce4e6f0c97dc437d96e53030c8cc822b
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

Loading…