Methane → HCID 12952973, compound

HRID 2413083Notes

Reaction equation

HRID 2413083 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[C:5]([Cl:10])=[CH:4][C:3]=1[NH:11][NH2:12].C(O[CH:16]=[C:17]([C:20]#[N:21])[C:18]#[N:19])C.C>CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+]>[NH2:21][C:20]1[N:11]([C:3]2[CH:4]=[C:5]([Cl:10])[C:6]([Cl:9])=[C:7]([Cl:8])[C:2]=2[Cl:1])[N:12]=[CH:16][C:17]=1[C:18]#[N:19]

Participants

6

Reactant 3

HCID 297MethaneHCID 671522-(Ethoxymethylene)propanedinitrileHCID 12952995HCID 12952995, compound

Product 1

HCID 12952973HCID 12952973, compoundYield 32.9%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateCatalystHCID 6228DimethylformamideSolvent

Procedure

2,3,4,5-Tetrachlorophenylhydrazine (12.3 g) was heated with ethoxymethylenemalononitrile (6.4 g) in dimethylformamide (25 ml) at reflux for 10 minutes in the presence of sodium carbonate (0.1 g). The hot solution was treated with charcoal and filtered and evaporated to dryness. The residue was triturated with diethyl ether and the ether solution was decanted and diluted with hexane to precipitate dark yellow crystals which were recrystallised from toluene to give 5-amino-4-cyano-1-(2,3,4,5-tetrachlorophenyl)pyrazole (5.3 g), m.p. 168°-169° C., in the form of off-white crystals.

Workup

  1. filtrationfiltered
  2. customevaporated to dryness
  3. customThe residue was triturated with diethyl ether
  4. customthe ether solution was decanted
  5. additiondiluted with hexane
  6. customto precipitate dark yellow crystals which
  7. customwere recrystallised from toluene

Sources & evidence

ORD record
ord-f4dd0da81c8e43fe9e29873b5d6fac4e
Source dataset
uspto-grants-1985_01
Patent number
US04496390

Reaction notes

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