Sodium Iodide → HCID 10830980, compound

HRID 1488492Notes

Reaction equation

HRID 1488492 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][N:11]2[CH:15]=[N:14][N:13]=[CH:12]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1)([O-:18])=[O:17].[I-].[Na+]>CC(=O)CC>[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:10]([N:11]2[CH:15]=[N:14][N:13]=[CH:12]2)[C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[CH:21][CH:20]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 660114-Nitrobenzyl bromideHCID 108458884-Nitrophenyl(1,2,4-triazol-4-yl)amine

Product 1

HCID 10830980HCID 10830980, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a suspension of 0.37 g of 4-[(4-nitrophenyl)amino]-4H-1,2,4-triazole obtained in Referential Example 3 in 20 ml of 2-butanone were successively added 0.83 g of potassium carbonate anhydride, 1.30 g of p-nitrobenzyl bromide and a catalytic amount of sodium iodide, at room temperature, and the reaction mixture was then heated under reflux for about 2 hours. After cooled, the solvent was removed by distillation under reduced pressure, and a proper amount of water was added to the residue, which was then extracted several times each with ethyl acetate. The ethyl acetate layer separated was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue formed was purified by silica gel column chromatography to give crude crystals from the chloroform/methanol (100/1) eluate. The crude crystals thus obtained were recrystallized from ethanol to give 0.28 g of 4-[N-(4-nitrobenzyl)-N-(4-nitrophenyl)amino]-4H-1,2,4-triazole.

Workup

  1. temperatureunder reflux for about 2 hours
  2. temperatureAfter cooled
  3. customthe solvent was removed by distillation under reduced pressure
  4. additiona proper amount of water was added to the residue, which
  5. extractionwas then extracted several times each with ethyl acetate
  6. customThe ethyl acetate layer separated
  7. washwas washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed by distillation under reduced pressure
  10. customThe residue formed
  11. customwas purified by silica gel column chromatography
  12. customto give crude crystals from the chloroform/methanol (100/1) eluate
  13. customThe crude crystals thus obtained
  14. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-35b8c72f4cb64491a0069754aec54fe5
Source dataset
uspto-grants-1997_10
Patent number
US05674886

Reaction notes

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