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

HRID 2413082Notes

Reaction equation

HRID 2413082 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)C>[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

4

Reactant 2

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

Product 1

HCID 30189015-amino-1-(2,3,4-trichlorophenyl)-1H-pyrazole-4-carbonitrileYield 43.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,3,4-Trichlorophenylhydrazine (21.15 g) was added in portions to a refluxing solution of ethoxymethylenemalononitrile (12.2 g) in ethanol (100 ml). The solution obtained was then heated at reflux for one hour, cooled and evaporated to dryness. The residue thus obtained was triturated with diethyl ether (100 ml) to give 5-amino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole (12.6 g), m.p. 158°-160° C., in the form of light brown crystals.

Workup

  1. customThe solution obtained
  2. temperaturewas then heated
  3. temperatureat reflux for one hour
  4. temperaturecooled
  5. customevaporated to dryness
  6. customThe residue thus obtained
  7. customwas triturated with diethyl ether (100 ml)

Sources & evidence

ORD record
ord-a61e8b70fc864e9abc69720a9cad9f98
Source dataset
uspto-grants-1985_01
Patent number
US04496390

Reaction notes

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