HCID 23035210, compound → HCID 23035214, compound

HRID 1710024Notes

Reaction equation

HRID 1710024 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:18]2[C:23](=[O:24])[NH:22][C:21](=[O:25])[CH:20]=[N:19]2)[CH:5]=[CH:6][C:7]=1[CH:8](Cl)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16].[Cu](C#N)[C:27]#[N:28]>ClC(Cl)Cl.CO>[Cl:1][C:2]1[CH:3]=[C:4]([N:18]2[C:23](=[O:24])[NH:22][C:21](=[O:25])[CH:20]=[N:19]2)[CH:5]=[CH:6][C:7]=1[CH:8]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])[C:27]#[N:28]

Participants

5

Reactant 2

HCID 23035210HCID 23035210, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 23035214HCID 23035214, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 12 parts of 2-[3-chloro-4-[chloro(2,4-dichlorophenyl)methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione and 5.4 parts of copper cyanide is stirred and heated first for 3 hours at 130° C. and for 3 hours at 180° C. After cooling, the precipitated product is dissolved in a mixture of trichloromethane and methanol (90:10 by volume). The inorganic precipitate is filtered off and the filtrate is evaporated in vacuo. The residue is purified by column chromatography over silica gel using first a mixture of trichloromethane and acetonitrile (93:7 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is dissolved in 20 parts of N,N-dimethylformamide and 25 parts of 1,1'-oxybisethane. The product is allowed to crystallize, filtered off and dried, yielding 2-chloro-α-(2,4-dichloro- phenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetonitrile (intermediate 1).

Workup

  1. temperatureAfter cooling
  2. filtrationThe inorganic precipitate is filtered off
  3. customthe filtrate is evaporated in vacuo
  4. customThe residue is purified by column chromatography over silica gel using first
  5. additiona mixture of trichloromethane and acetonitrile (93:7 by volume) as eluent
  6. customThe pure fractions are collected
  7. customthe eluent is evaporated
  8. dissolutionThe residue is dissolved in 20 parts of N,N-dimethylformamide and 25 parts of 1,1'-oxybisethane
  9. customto crystallize
  10. filtrationfiltered off
  11. customdried

Sources & evidence

ORD record
ord-ddaff90f0d1047a9baadde578ab5f7bf
Source dataset
uspto-grants-1990_08
Patent number
US04952570

Reaction notes

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