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

HRID 1376378

Reaction equation

HRID 1376378 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-2f43627d002d44e28d7c8767ab798787
Source dataset
uspto-grants-1997_09
Patent number
US05663053

Linked notes

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