Water → 1-(4-Nitrophenyl)-1H-1,2,4-triazole

HRID 2392670Notes

Reaction equation

HRID 2392670 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[N:11]1([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH:15]=[N:14][CH:13]=[N:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 110953981-(4-Nitrophenyl)-1H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

4Fluoronitrobenzene (2 g, 0.014 mol), 1,2,4-triazole (1 g, 0.014 mol), potassium carbonate (1.96 g, 0.014 mol) were dissolved in DMSO (50 ml) and stirred at 90° C. for 24 h under dry conditions. The yellow suspension was poured into water (150 ml), extracted (EtOAc), dried (Na2SO4) and evaporated under reduced pressure to afford an orange solid which was purified by flash column chromatography on silica eluting with n-pentane/ethyl acetate (50-100%) to afford a white solid (2.57 g 97%).

Workup

  1. extractionextracted (EtOAc)
  2. dry with materialdried (Na2SO4)
  3. customevaporated under reduced pressure
  4. customto afford an orange solid which
  5. customwas purified by flash column chromatography on silica eluting with n-pentane/ethyl acetate (50-100%)
  6. customto afford a white solid (2.57 g 97%)

Sources & evidence

ORD record
ord-a98078005de946f7bbb9ee7c31a04b54
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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