1,3,5-Triazine → 1-(3-Nitrophenyl)-1H-1,2,4-triazole

HRID 2086798Notes

Reaction equation

HRID 2086798 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([NH:11][NH2:12])[CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3].[N:13]1[CH:18]=NC=N[CH:14]=1.C(=O)(O)[O-].[Na+]>C(O)C>[N+:2]([C:5]1[CH:6]=[C:7]([N:11]2[CH:18]=[N:13][CH:14]=[N:12]2)[CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 92621,3,5-TriazineHCID 516892Sodium BicarbonateHCID 54642853-Nitrophenylhydrazinium(1+) chloride

Product 1

HCID 149508381-(3-Nitrophenyl)-1H-1,2,4-triazoleYield 49.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-nitrophenylhydrazine hydrochloride (8.77 g) and 1,3,5-triazine (2.50 g) in ethanol (40 ml) was stirred under reflux for 4 hours. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column (hexane-ethyl acetate, 3:7) to give 1-(3-nitrophenyl)-1H-1,2,4-triazole (2.89 g) as a solid.

Workup

  1. temperatureunder reflux for 4 hours
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel column (hexane-ethyl acetate, 3:7)

Sources & evidence

ORD record
ord-cc6b3a560c9b40168ddbcd3fe480e95b
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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