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

HRID 369180Notes

Reaction equation

HRID 369180 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-b58e6b6410494dc2a004a63ddfa11be4
Source dataset
uspto-grants-2000_10
Patent number
US06136826

Reaction notes

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