Acetic Anhydride → 4-[N-(4-acetylaminophenyl)-N-(4-bromobenzyl)amino]-4H-1,2,4-triazole

HRID 1488509Notes

Reaction equation

HRID 1488509 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([N:24]2[CH:28]=[N:27][N:26]=[CH:25]2)[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)=[CH:11][CH:10]=1>N1C=CC=CC=1>[C:5]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([N:24]2[CH:25]=[N:26][N:27]=[CH:28]2)[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([Br:23])=[CH:21][CH:22]=2)=[CH:11][CH:10]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 229058094-[N-(4-aminophenyl)-N-(4-bromobenzyl)amino]-4H-1,2,4-triazole

Product 1

HCID 229057974-[N-(4-acetylaminophenyl)-N-(4-bromobenzyl)amino]-4H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.28 Milliliter of acetic anhydride was added to ml of a pyridine solution containing 0.35 g of 4-[N-(4-aminophenyl)-N-(4-bromobenzyl)amino]-4H-1,2,4-triazole at room temperature and the mixture was stirred for about minutes. After reaction, the solvent was removed by distillation under reduced pressure, and a proper amount of an aqueous sodium hydrogen carbonate solution was added to the resulting residue, which was then extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel chromatography to obtain 0.33 g of 4-[N-(4-acetylaminophenyl)-N-(4-bromobenzyl)amino]-4H-1,2,4-triazole from the chloroform/methanol (50/1) eluate.

Workup

  1. customAfter reaction
  2. customthe solvent was removed by distillation under reduced pressure
  3. additiona proper amount of an aqueous sodium hydrogen carbonate solution was added to the resulting residue, which
  4. extractionwas then extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6252e39343ae4ecb8341066955ef80d5
Source dataset
uspto-grants-1997_10
Patent number
US05674886

Reaction notes

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