Potassium Carbonate → HCID 9951467, compound

HRID 1488493Notes

Reaction equation

HRID 1488493 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].[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][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:19][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 108458884-Nitrophenyl(1,2,4-triazol-4-yl)amine

Product 1

HCID 9951467HCID 9951467, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8 Milliliters of acetonitrile was added to 0.63 g of 4-[N-(4-nitrophenyl)amino]-4H-1,2,4-triazole, 0.82 g of 4-bromobenzyl bromide and 0.62 g of anhydrous potassium carbonate and the mixture was stirred for 3 hours at room temperature. The solvent was removed by distillation under reduced pressure, and water was added to the residue obtained, which was then extracted with chloroform. The chloroform layer separated was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography to give crude crystals from the chloroform/methanol (100/1) eluate. The crude crystals were recrystallized from acetone to give 0.71 g of 4-[N-(4-bromobenzyl)-N-(4-nitrophenyl)amino]-4H-1,2,4-triazole.

Workup

  1. customThe solvent was removed by distillation under reduced pressure, and water
  2. additionwas added to the residue
  3. customobtained
  4. extractionwhich was then extracted with chloroform
  5. customThe chloroform layer separated
  6. washwas washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed by distillation
  9. customThe residue was purified by silica gel column chromatography
  10. customto give crude crystals from the chloroform/methanol (100/1) eluate
  11. customThe crude crystals were recrystallized from acetone

Sources & evidence

ORD record
ord-1a6bf35e835e4c4390528c86befa43bd
Source dataset
uspto-grants-1997_10
Patent number
US05674886

Reaction notes

Loading…