1H-1,2,4-Triazole → 3-(1H-1,2,4-triazol-1-yl)propan-1-ol

HRID 454111Notes

Reaction equation

HRID 454111 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[O-]CC.[Na+].[Na].Br[CH2:12][CH2:13][CH2:14][OH:15]>C(O)C>[N:1]1([CH2:12][CH2:13][CH2:14][OH:15])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 123083-Bromo-1-propanolHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 47118023-(1H-1,2,4-triazol-1-yl)propan-1-olYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under argon, 1,2,4-triazole (13.8 g, 200 mmol) was added to a solution of sodium ethoxide (freshly prepared from sodium (4.6 g) and ethanol (250 ml)). After complete dissolution, 3-bromopropan-1-ol (18 ml, 200 mmol) was added dropwise. The mixture was refluxed for 18 hours and the solid was filtered and washed with ethanol. The filtrate was evaporated and the residue was purified by column chromatography eluting with methylene chloride/methanol (9/1) to give 3-(1,2,4-triazol-1-yl)propan-1-ol (22.8 g, 90%).

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was refluxed for 18 hours
  3. filtrationthe solid was filtered
  4. washwashed with ethanol
  5. customThe filtrate was evaporated
  6. customthe residue was purified by column chromatography
  7. washeluting with methylene chloride/methanol (9/1)

Sources & evidence

ORD record
ord-38c395345226470aaf290d9d61a87b36
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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