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

HRID 2392651Notes

Reaction equation

HRID 2392651 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-])N.[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 949565-Fluoro-2-nitrotolueneHCID 23668002Potassium carbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-fluoro-2-methylnitrobenzene (2 g), 1,2,4-triazole (0.9 g) and anhydrous potassium carbamate (1.78 g) was stirred and heated in dimethylsulphoxide (50 ml) at 90° C. for 24 hours. The reaction mixture was cooled, poured into water (200 ml) and extracted with ethyl acetate. The ethyl acetate layer was separated, dried (MgSO4) and evaporated to give an orange solid which was purified by chromatography on silica using pentane/ethyl acetate as eluant, (1.8 g, 69%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give an orange solid which
  7. customwas purified by chromatography on silica

Sources & evidence

ORD record
ord-f9e6188675f84b12aff75eafdf396a33
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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