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

HRID 128458Notes

Reaction equation

HRID 128458 reaction equation
[F: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]([F: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 40619641-(p-Fluorophenyl)-5-(p-nitrophenyl)-1H-1,2,4-triazole

Product 1

HCID 126766705-(p-Aminophenyl)-1-(p-fluorophenyl)-1H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 9.0 g. of 1-(p-fluorophenyl)-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 for 1/2 hour. The acetone is removed in vacuo and the residue extracted with hot chloroform. Cooling produces 1.1 g. of the desired product as off-white crystals, mp. 128°-130° C.

Workup

  1. additionA mixture of 9.0 g
  2. customThe acetone is removed in vacuo
  3. extractionthe residue extracted with hot chloroform
  4. temperatureCooling
  5. customproduces 1.1 g

Sources & evidence

ORD record
ord-8582b7435b424ed28897f18fc6e6902c
Source dataset
uspto-grants-1981_03
Patent number
US04259504

Reaction notes

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