Sodium hydride → HCID 22618395, compound

HRID 842163Notes

Reaction equation

HRID 842163 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][NH2:14].[C:15]([C:17]([C:24]#[N:25])=[C:18]([CH:21]1[CH2:23][CH2:22]1)OC)#[N:16].[H-].[Na+]>CO>[NH2:25][C:24]1[N:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:5][C:4]=2[Cl:12])[N:14]=[C:18]([CH:21]2[CH2:23][CH2:22]2)[C:17]=1[C:15]#[N:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 22618537HCID 22618537, compound

Product 1

HCID 22618395HCID 22618395, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,6-dichloro-4-trifluoromethylphenylhydrazine (3.8 g) and 1,1-dicyano-2-cyclopropyl-2-methoxyethylene (2.23 g) in methanol (30 ml) was stirred and treated with sodium hydride (80%, 30 mg). After 4 hours the solution was evaporated in vacuo and the residue was dissolved in ethyl acetate (40 ml), treated with charcoal and washed with water. The organic phase was evaporated in vacuo, the residual oil was dissolved in petroleum ether and crystals of 5-amino-4-cyano-3-cyclopropyl-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole, m.p. 197-199° C., were obtained.

Workup

  1. customAfter 4 hours the solution was evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (40 ml)
  3. additiontreated with charcoal
  4. washwashed with water
  5. customThe organic phase was evaporated in vacuo
  6. dissolutionthe residual oil was dissolved in petroleum ether

Sources & evidence

ORD record
ord-2a6589d93d3349c89bceae88cda73a8e
Source dataset
uspto-grants-2002_04
Patent number
US06372774B1

Reaction notes

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