Water → N-[2-(4-chlorophenoxy)-1-(4-fluorophenyl)ethylidene]-1H-1,2,4-triazol-1-amine

HRID 2248610Notes

Reaction equation

HRID 2248610 reaction equation
[NH2:1][N:2]1[CH:6]=[N:5][CH:4]=[N:3]1.[Cl:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=O)=[CH:10][CH:9]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][C:14](=[N:1][N:2]2[CH:6]=[N:5][CH:4]=[N:3]2)[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 80030362-(4-Chlorophenoxy)-4'-fluoroacetophenoneHCID 117080471H-1,2,4-triazol-1-amine

Product 1

HCID 54205763N-[2-(4-chlorophenoxy)-1-(4-fluorophenyl)ethylidene]-1H-1,2,4-triazol-1-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 1-amino-1H-1,2,4-triazole (75% purity, 5.6 g, 0.05 mmol) and 2-(4-chlorophenoxy)-4'-fluoroacetophenone (13.2 g, 0.05 mmol) in 100 mL dry toluene is added a catalytic amount (1.0 g) p-toluene sulfonic acid. The mixture is heated at reflux with azeotropic removal of water for 4 days. Solvent is evaporated and the residue taken up in 200 mL ethyl acetate. The organic solution is washed with 2×100 mL 10% aqueous Na2CO3 and 1×100 mL brine. The dried (MgSO4) solution is filtered and concentrated to give the desired product which can be purified by chromatography or crystallization from an appropriate solvent.

Workup

  1. temperatureThe mixture is heated
  2. customSolvent is evaporated
  3. washThe organic solution is washed with 2×100 mL 10% aqueous Na2CO3 and 1×100 mL brine
  4. dry with materialThe dried (MgSO4) solution
  5. filtrationis filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-58ea327f695b487c9a7cea2a82d4b240
Source dataset
uspto-grants-1991_08
Patent number
US05041458

Reaction notes

Loading…