Water → 3-Fluoro-1-nitro-4-(1H-1,2,4-triazol-1-yl)benzene

HRID 1955109Notes

Reaction equation

HRID 1955109 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[F:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1F.O>CS(C)=O>[F:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1[N:1]1[CH:5]=[N:4][CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 62657Potassium Phosphate, TribasicHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 53061543-Fluoro-1-nitro-4-(1H-1,2,4-triazol-1-yl)benzeneYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 5.0 g(72.4 mmol) of 1H-1,2,4-triazol and 25.22 g(144.8 mmol) of dibasic potassium phosphate in 150 mL DMSO was treated with 11.52 g(72.4 mmol) of 3,4-difluoronitrobenzene followed by warming at 90° C. for 3 h. The solution was cooled and added to 500 mL water, and the resulting white solid was collected by filtration and washed with water. The white solid obtained was dried in vacuo (60° C./10 mmHg) to afford 10.79 g(72%) of the title compound as a white solid. High Resolution Mass Spectrum: Calculated for C8H5FN4O2 : 208.0396. Found: 208.0408.

Workup

  1. temperatureThe solution was cooled
  2. filtrationthe resulting white solid was collected by filtration
  3. washwashed with water
  4. customThe white solid obtained
  5. customwas dried in vacuo (60° C./10 mmHg)

Sources & evidence

ORD record
ord-4a1b9cfa8c3c49f6aa1065a4c6a0f344
Source dataset
uspto-grants-2000_09
Patent number
US06124334

Reaction notes

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