Dimethylformamide dimethyl acetal → 1-(p-Fluorophenyl)-5-[p-[(dimethylaminomethylene)amino]phenyl]-1H-1,2,4-triazole

HRID 128459Notes

Reaction equation

HRID 128459 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.CO[CH:22](OC)[N:23]([CH3:25])[CH3:24]>CO>[F:19][C:16]1[CH:17]=[CH:18][C:13]([N:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:1]=[CH:22][N:23]([CH3:25])[CH3:24])=[CH:3][CH:4]=3)=[N:9][CH:10]=[N:11]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 126766705-(p-Aminophenyl)-1-(p-fluorophenyl)-1H-1,2,4-triazole

Product 1

HCID 234697261-(p-Fluorophenyl)-5-[p-[(dimethylaminomethylene)amino]phenyl]-1H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5.0 g. of 5-(p-aminophenyl)-1-(p-fluorophenyl)-1H-1,2,4-triazole in 20 ml. of dimethylformamide dimethylacetal is heated to reflux for 1.5 hours while the methanol formed is collected by distillation. The reaction mixture is cooled, 15 ml. of ether is added and the mixture is cooled further, giving 5.5 g. of the desired product, mp. 159°-161° C.

Workup

  1. customformed
  2. distillationis collected by distillation
  3. temperatureThe reaction mixture is cooled
  4. additionof ether is added
  5. temperaturethe mixture is cooled further
  6. customgiving 5.5 g

Sources & evidence

ORD record
ord-9bf6425475514e9bb40c68dc10b0cad5
Source dataset
uspto-grants-1981_03
Patent number
US04259504

Reaction notes

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