2-(Ethoxymethylene)propanedinitrile → 5-amino-1-(2,3,4-trichlorophenyl)-1H-pyrazole-4-carbonitrile

HRID 2413084Notes

Reaction equation

HRID 2413084 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(OC(O)C)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 2

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

Product 1

HCID 30189015-amino-1-(2,3,4-trichlorophenyl)-1H-pyrazole-4-carbonitrileYield 52.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 101298981-EthoxyethanolSolvent

Procedure

2,3,4-Trichlorophenylhydrazine (21.15 g) and ethoxymethylenemalononitrile (12.8 g) in ethoxyethanol (100 ml) were heated at reflux for one hour. The solution was then cooled and diluted with water. The sticky solid precipitate thus obtained was crystallized from toluene (48 ml) to give 5-amino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole (15 g), m.p. 154°-156° C., in the form of off-white crystals.

Workup

  1. temperatureat reflux for one hour
  2. temperatureThe solution was then cooled
  3. customThe sticky solid precipitate thus obtained
  4. customwas crystallized from toluene (48 ml)

Sources & evidence

ORD record
ord-b5e57a8ee485449bb56c7368f6336246
Source dataset
uspto-grants-1985_01
Patent number
US04496390

Reaction notes

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