1H-1,2,4-Triazole → Ethyl 4-(4H-1,2,4-triazol-4-yl)benzoate

HRID 278558Notes

Reaction equation

HRID 278558 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[NH:13]1[CH:17]=[N:16][CH:15]=[N:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:13]1([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH:17]=[N:16][CH:15]=[N:14]1.[N:13]1[N:14]=[CH:15][N:16]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH:17]=1

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

Product 2

HCID 22627983Ethyl 4-(4H-1,2,4-triazol-4-yl)benzoateHCID 22628005Ethyl 4-(1H-1,2,4-triazol-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 4-fluorobenzoate (8.4 g), 1,2,4-triazole (4.14 g) and potassium carbonate (20.7 g) in DMF (30 ml) was stirred at 100° C. for 3 hours and concentrated. To the residue was added dichloromethane, and the mixture was washed with water, dried and concentrated. The residue was purified with silica gel column chromatography (dichloromethane:methanol=50:1→20:1) to give a colorless solid of ethyl 4-(1,2,4-triazol-1-yl)benzoate (4.0 g) and ethyl 4-(1,2,4- triazol-4- yl)benzoate (369 mg).

Workup

  1. concentrationconcentrated
  2. additionTo the residue was added dichloromethane
  3. washthe mixture was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography (dichloromethane:methanol=50:1→20:1)

Sources & evidence

ORD record
ord-83dd8672aff746f49b3259f39b99b93d
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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