Acetonitrile → methyl 1-benzyl-1H-1,2,4-triazole-3-carboxylate

HRID 491892Notes

Reaction equation

HRID 491892 reaction equation
[N:1]1[N:2]([C:6](OC)=O)[CH:3]=[N:4][CH:5]=1.C(Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:18](=[O:21])([O-])[O-:19].[K+].[K+].[C:24](#N)C>>[CH3:24][O:19][C:18]([C:5]1[N:4]=[CH:3][N:2]([CH2:6][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:1]=1)=[O:21]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 642208methyl 1H-1,2,4-triazole-1-carboxylate

Product 1

HCID 67023628methyl 1-benzyl-1H-1,2,4-triazole-3-carboxylate

Procedure

A solution of methyl 1,2,4-triazole-2-carboxylate (6.89 g, 54.2 mmole), benzyl bromide (7.7 mL, 65.0 mmol) and potassium carbonate (11.24 g, 81.3 mmol) in acetonitrile (100 mL) was refluxed overnight. The solution was then filtered and concentrated to a residue. The residue was dissolved in diethyl ether. The solution washed with 1N sodium hydroxide one time and water one time, and then dried over MgSO4. The solution was filtered and concentrated to yield 1-benzyl-1H-[1,2,4]triazole-3-carboxylic acid methyl ester as a brown oil, which was used in next step without further purification.

Workup

  1. filtrationThe solution was then filtered
  2. concentrationconcentrated to a residue
  3. dissolutionThe residue was dissolved in diethyl ether
  4. washThe solution washed with 1N sodium hydroxide one time and water one time
  5. dry with materialdried over MgSO4
  6. filtrationThe solution was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3f7ccd8f78dc45109610f39641ee36b2
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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