Sodium hydride → HCID 22618395, compound

HRID 975524Notes

Reaction equation

HRID 975524 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-79a6cf282d1a4a92a5e22a6a76c9e4d1
Source dataset
uspto-grants-1997_03
Patent number
US05608077

Reaction notes

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