Water → 5-(p-Aminophenyl)-1-(p-bromophenyl)-1H-1,2,4-triazole

HRID 128456Notes

Reaction equation

HRID 128456 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)=[N:11][CH:10]=[N:9]2)=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].O>CC(C)=O>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)[N:9]=[CH:10][N:11]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24489Sodium DithioniteHCID 12676668HCID 12676668, compound

Product 1

HCID 126766735-(p-Aminophenyl)-1-(p-bromophenyl)-1H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 9.0 g. of 1-(p-bromophenyl)-5-(p-nitrophenyl)-1H-1,2,4-triazole, 18.0 g. of sodium hydrosulfite, 40 ml. of water and 150 ml. of acetone is stirred at room temperature overnight. The acetone is removed in vacuo and the residue is extracted with hot chloroform. Cooling produces 2.1 g. of the desired product as pale yellow crystals, mp. 128°-130° C.

Workup

  1. additionA mixture of 9.0 g
  2. customThe acetone is removed in vacuo
  3. extractionthe residue is extracted with hot chloroform
  4. temperatureCooling
  5. customproduces 2.1 g

Sources & evidence

ORD record
ord-01176273fad3487795740cd5ce94da69
Source dataset
uspto-grants-1981_03
Patent number
US04259504

Reaction notes

Loading…