Water → 1-(3-Methyl-4-nitrophenyl)-1,2,4-triazole

HRID 2392677Notes

Reaction equation

HRID 2392677 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=1.[NH:12]1[CH:16]=[N:15][CH:14]=[N:13]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:11][C:4]1[CH:3]=[C:2]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 144502481-(3-Methyl-4-nitrophenyl)-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

4-Fluoro-2-methyl-nitrobenzene (2 g, 0.013 mol), 1,2,4-triazole (0.9 g, 0.013 mol), potassium carbonate (1.78 g, 0.013 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 (2.83 g 69%).

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 (2.83 g 69%)

Sources & evidence

ORD record
ord-b953e436c2f84634be2be7b13e0bbc25
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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