Acetic Acid → 5-amino-1-(2,3,4-trichlorophenyl)-1H-pyrazole-4-carbonitrile

HRID 1284399Notes

Reaction equation

HRID 1284399 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[NH:10][NH2:11].C(O[CH:15]=[C:16]([C:19]#[N:20])[C:17]#[N:18])C.C(O)(=O)C>O>[NH2:20][C:19]1[N:10]([C:3]2[CH:4]=[CH:5][C:6]([Cl:9])=[C:7]([Cl:8])[C:2]=2[Cl:1])[N:11]=[CH:15][C:16]=1[C:17]#[N:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 671522-(Ethoxymethylene)propanedinitrileHCID 129529942,3,4-Trichlorophenylhydrazine

Product 1

HCID 30189015-amino-1-(2,3,4-trichlorophenyl)-1H-pyrazole-4-carbonitrileYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 15 g of 2,3,4-trichlorophenylhydrazine, 8.7 g of (ethoxymethylene)malononitrile, 100 ml of glacial acetic acid and 50 ml of water was refluxed for 3 hours. The reaction mixture was cooled, poured into ice water and the precipitated solid was collected by filtration and dried. This solid was dissolved in ethyl acetate and the resulting solution was washed twice with saturated sodium bicarbonate, once with 100 ml of water, once with 100 ml of saturated brine and dried over anhydrous magnesium sulfate. The organic phase was evaporated under reduced pressure and the residue was recrystallized from ethanol to give 13.2 g of 5-amino-1-(2,3,4-trichlorophenyl)-1H-pyrazole-4-carbonitrile. Yield 66%. mp=140°-142° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe precipitated solid was collected by filtration
  3. customdried
  4. dissolutionThis solid was dissolved in ethyl acetate
  5. washthe resulting solution was washed twice with saturated sodium bicarbonate, once with 100 ml of water, once with 100 ml of saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe organic phase was evaporated under reduced pressure
  8. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-6f3bc84fa9d348b1bf901321a6f80e36
Source dataset
uspto-grants-1986_01
Patent number
US04563210

Reaction notes

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