Ethyl Acetate → 1-(4-Methoxybenzyl)-1,2,4-triazole

HRID 610622Notes

Reaction equation

HRID 610622 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[OH-].[Na+].[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][CH:11]=1.C(OCC)(=O)C>CN(C)C=O.O>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 92571H-1,2,4-TriazoleHCID 14798Sodium HydroxideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 108453281-(4-Methoxybenzyl)-1,2,4-triazoleYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

1,2,4-Triazole (7.5 g, 0.109 mol) was dissolved in dimethylformamide (50 mL) and stirred under a nitrogen atmosphere in an ice bath at 10° C. while partially ground pellets of sodium hydroxide (17.5 g, 0.438 mol) were added in one portion causing an exotherm to about 25° C. A solution of 4-methoxybenzyl chloride (15 mL, 0.111 mol) in DMF was added dropwise over five minutes at 25° C. After stirring at room temperature for four hours, ethyl acetate and water were added. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed four times with water and once with brine and dried over magnesium sulfate. The mixture was filtered and the filtrate solvent evaporated in vacuo to afford the title product as an oil in 69% yield; 14.15 g; 1H NMR (CDCl3) δ 8.00 (s, 1), 7.93 (s, 1), 7.19 (d, 2), 6.88 (d, 2), 5.23 (s, 2), 3.78 (s, 3). mass spectrum: m/z 109 (M+1).

Workup

  1. additionwere added in one portion
  2. customto about 25° C
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed four times with water
  6. dry with materialonce with brine and dried over magnesium sulfate
  7. filtrationThe mixture was filtered
  8. customthe filtrate solvent evaporated in vacuo

Sources & evidence

ORD record
ord-1828e18fd7864d4eae77a36447b9de93
Source dataset
uspto-grants-1999_12
Patent number
US05998623

Reaction notes

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