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

HRID 355737Notes

Reaction equation

HRID 355737 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.F[C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[N:1]1([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

Product 1

HCID 22628005Ethyl 4-(1H-1,2,4-triazol-1-yl)benzoateYield 73.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

1,2,4-Triazole (0.82 g, 0.01 mol), ethyl 4-fluorobenzoate (2 g, 0.01 mol) and anhydrous potassium carbonate (1.43 g, 0.01 mol) was dissolved in DMSO (30 ml) and heated to 90° C. for 18 h. The solution was poured into water (50 ml), extracted with ethyl acetate (50 ml), dried (sodium sulphate), filtered and evaporated to dryness under reduced pressure. The white solid was purified by flash column chromatography (silica, diethyl ether) to afford a white solid (1.59 g, 73%).

Workup

  1. extractionextracted with ethyl acetate (50 ml)
  2. dry with materialdried (sodium sulphate)
  3. filtrationfiltered
  4. customevaporated to dryness under reduced pressure
  5. customThe white solid was purified by flash column chromatography (silica, diethyl ether)

Sources & evidence

ORD record
ord-044a82c45c654a089ad860363c8e8202
Source dataset
uspto-grants-1998_11
Patent number
US05834471

Reaction notes

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