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

HRID 2257140Notes

Reaction equation

HRID 2257140 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C(#N)C>[N:1]1([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 3832489Benzyl 4-bromobutanoate

Product 1

HCID 10490579Benzyl 4-(1,2,4-triazol-1-yl)butyrateYield 81.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.7 g of 1,2,4-triazole and 9.5 g of potassium carbonate were added to a solution of 15 g of benzyl 4-bromobutyrate in 150 ml of acetonitrile. The mixture was refluxed by heating, for 1 hour. The reaction mixture was concentrated under reduced pressure. To the residue was added 30 ml of methylene chloride. The insolubles were collected by filtration and washed. The filtrate and the washings were combined and purified by silica gel column chromatography (eluant: methylene chloride/methanol=50/1) to obtain 11.6 g of benzyl 4-(1,2,4-triazol-1-yl)butyrate as a colorless oily substance.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureby heating, for 1 hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionTo the residue was added 30 ml of methylene chloride
  5. filtrationThe insolubles were collected by filtration
  6. washwashed
  7. custompurified by silica gel column chromatography (eluant: methylene chloride/methanol=50/1)

Sources & evidence

ORD record
ord-841fdb412580443ba1fdd649fef8d35b
Source dataset
uspto-grants-1997_08
Patent number
US05656642

Reaction notes

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