Tetracyanoethylene → HCID 22618603, compound

HRID 1078447Notes

Reaction equation

HRID 1078447 reaction equation
C([C:3]([C:9]#[N:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6])#N.[Cl:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([Cl:22])[C:13]=1[NH:23][NH2:24].C([O-])(=O)C.[Na+]>C(O)(=O)C>[NH2:8][C:7]1[N:23]([C:13]2[C:14]([Cl:22])=[CH:15][C:16]([C:18]([F:19])([F:20])[F:21])=[CH:17][C:12]=2[Cl:11])[N:24]=[C:3]([C:9]#[N:10])[C:4]=1[C:5]#[N:6]

Participants

5

Reactant 3

HCID 12635TetracyanoethyleneHCID 517045Sodium AcetateHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine

Product 1

HCID 22618603HCID 22618603, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Tetracyanoethylene (1.9 g) and 2,6-dichloro-4-trifluoromethylphenylhydrazine (3.7 g) was added to a magnetically-stirred solution of sodium acetate (0.6 g) in glacial acetic acid (15 ml) at laboratory temperature. After stirring for 15 minutes, a colorless solid precipitated from the solution and stirring was continued overnight. The mixture was then filtered. The solid obtained was washed successively with acetic acid, water, aqueous sodium bicarbonate solution and water, to give 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3,4-dicyanopyrazole (2.5 g), as beige crystals, m.p. 221°-222° C.

Workup

  1. customa colorless solid precipitated from the solution
  2. stirringstirring
  3. waitwas continued overnight
  4. filtrationThe mixture was then filtered
  5. customThe solid obtained
  6. washwas washed successively with acetic acid, water, aqueous sodium bicarbonate solution and water

Sources & evidence

ORD record
ord-7fc52d173ccd47e7a21c6ada372c3348
Source dataset
uspto-grants-1996_08
Patent number
US05547974

Reaction notes

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