Tetracyanoethylene → HCID 22618603, compound

HRID 842151Notes

Reaction equation

HRID 842151 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-trifluoromethylphenyl hydrazine (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-8f31297bcf3a47d187031ba0f699cab5
Source dataset
uspto-grants-2002_04
Patent number
US06372774B1

Reaction notes

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