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

HRID 865700Notes

Reaction equation

HRID 865700 reaction equation
[Na].[NH:2]1[CH:6]=[N:5][CH:4]=[N:3]1.F[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.O.C(OCC)(=O)C>CN(C=O)C>[N:2]1([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[CH:6]=[N:5][CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 9590p-FluoronitrobenzeneHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 110953981-(4-Nitrophenyl)-1H-1,2,4-triazoleYield 72.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2,4-Triazole sodium derivative (90%) (17.74 g, 0.18 mol) and 1-fluoro-4-nitrobenzene (25 g, 0.18 mol), in DMF, (150 ml) was stirred at room temperature for 4 days. Water (300 ml) and ethyl acetate (500 ml) were added and the mixture extracted. The organic layer was separated, washed with water (3×300 ml), dried (MgSO4) and evaporated to give the desired product (24.8 g); δ (360 MHz, CDCl3) 7.92 (2H, d, J=9.1 Hz, Ar--H); 8.17 (1H, s, Ar--H); 8.40.(2H, d, J=9.1 Hz, Ar--H); 8.48 (1H, s, Ar--H).

Workup

  1. extractionthe mixture extracted
  2. customThe organic layer was separated
  3. washwashed with water (3×300 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-a285481390734b4ca67e23e2c926e6ac
Source dataset
uspto-grants-1996_10
Patent number
US05567726

Reaction notes

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