Tetracyanoethylene → HCID 22618603, compound

HRID 975512Notes

Reaction equation

HRID 975512 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-cb4a252f76c04f949ac0bca38f195acd
Source dataset
uspto-grants-1997_03
Patent number
US05608077

Reaction notes

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