1H-1,2,4-Triazole → 4-(1H-1,2,4-triazol-1-yl)benzaldehyde

HRID 1941344Notes

Reaction equation

HRID 1941344 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].F[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1>N1C=CC=CC=1.[Cu-]=O>[N:1]1([C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 27764884-(1H-1,2,4-triazol-1-yl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 1,2,4-triazole (4.06 g, 58.7 mmol), potassium carbonate (9.05 g, 65.5 mmol), 4-fluorobenzaldehyde (6.3 ml, 58.7 mmol), and copper(I) oxide (0.26 g, 1.82 mmol) in pyridine (30 ml) is heated under nitrogen atmosphere at reflux overnight. After pyridine is distilled, the residue is diluted with chloroform, filtered, and washed with chloroform. The combined filtrate is washed with water, dried over magnesium sulfate, and concentrated in vacuo. The crude material is purified by column chromatography on silica with hexane/ethyl acetate (1:2) to give 4-(1,2,4-triazol-1-yl)-benzaldehyde and with ethyl acetate/methanol (19:1) to give 4-(1,3,4-triazol-1-yl)-benzaldehyde.

Workup

  1. temperatureis heated under nitrogen atmosphere
  2. temperatureat reflux overnight
  3. distillationAfter pyridine is distilled
  4. additionthe residue is diluted with chloroform
  5. filtrationfiltered
  6. washwashed with chloroform
  7. washThe combined filtrate is washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe crude material is purified by column chromatography on silica with hexane/ethyl acetate (1:2)

Sources & evidence

ORD record
ord-98f2a17d58444bc39103f80ee88276d3
Source dataset
uspto-grants-1997_12
Patent number
US05703106

Reaction notes

Loading…