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

HRID 1780911Notes

Reaction equation

HRID 1780911 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][CH:11]=1>CN(C=O)C>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:3]2[CH:7]=[N:6][CH:5]=[N:4]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 108453281-(4-Methoxybenzyl)-1,2,4-triazoleYield 79.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 4 g (0.16 mol) of sodium hydride in 200 ml of DMF 20 at 0° C. was added 10 g (0.145 mol) of 1,2,4-triazole in 75 ml of DMF dropwise over a period of 30 minutes, and the mixture was allowed to warm to room temperature and stirred for 1 h. The above mixture was cooled to 0° C., 25 g (0.16 mol) of p-methoxybenzyl chloride was added, the mixture was allowed to warm to room temperature, and stirred for 16 h. The reaction mixture was concentrated in vacuo and the residue was purified by chromatography on silica (hexane/ethyl acetate) to afford 21.9 g (64.5%) of 1-(p-methoxybenzyl)-1,2,4-triazole.

Workup

  1. temperatureThe above mixture was cooled to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for 16 h
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe residue was purified by chromatography on silica (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6384099966cc470f9da8fd1817c1ceaf
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

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