1H-1,2,4-Triazole → 1-(4-Methoxybenzyl)-1,2,4-triazole

HRID 748061Notes

Reaction equation

HRID 748061 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[CH3:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Cl)=[CH:10][CH:9]=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[CH3:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 699934-Methyloxybenzyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 108453281-(4-Methoxybenzyl)-1,2,4-triazoleYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1,2,4-triazole (2.0 g, 29 mmol) in THF (80 mL) at 0° C. was added 4-methoxybenzyl chloride (4.0 mL, 29 mmol) and DBU (5.20 mL, 34.7 mmol). The reaction mixture was warmed to room temperature and allowed to stir overnight. The solution was filtered and the filtrate was concentrated. The resulting residue was purified by column chromatography (EtOAc/MeOH, 1:9) to give 3.12 g (57%) of 1-(4-methoxybenzyl)-1H-1,2,4-triazole as a colorless oil.

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was purified by column chromatography (EtOAc/MeOH, 1:9)

Sources & evidence

ORD record
ord-ad67110a16d7408c8de6eff2bf355f35
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

Loading…