Chloroform → HCID 20296005, compound

HRID 1389936Notes

Reaction equation

HRID 1389936 reaction equation
Cl[C:2]([C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:18])=[N:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10].ClC(Cl)Cl.[C-:23]#[N:24].[K+]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[C:2](=[N:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])[C:23]#[N:24]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 9032Potassium CyanideHCID 20296029HCID 20296029, compound

Product 1

HCID 20296005HCID 20296005, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a stirred solution of 7.45 parts of N-[chloro(2,6-dichlorophenyl)methylene]-2-methylbenzenamine in 150 parts of trichloromethane is added a solution of 4.88 parts of potassium cyanide and 8.5 parts of N,N,N-triethylbenzenemethanaminium chloride in 8 parts of water while stirring vigorously. Stirring is continued for 30 minutes at room temperature. The organic phase is separated, washed twice with water, dried, filtered and evaporated. The residue is dissolved in petroleumether and the solution is decanted from some insoluble tar. The petroleumether is evaporated in vacuo. The residue is purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 17.5 parts of petroleumether, yielding 2.8 parts of 2,6-dichloro-α-[(2-methylphenyl)imino]benzeneacetonitrile; mp. 55° C.

Workup

  1. stirringStirring
  2. customThe organic phase is separated
  3. washwashed twice with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe residue is dissolved in petroleumether
  8. customthe solution is decanted from some insoluble tar
  9. customThe petroleumether is evaporated in vacuo
  10. customThe residue is purified by column-chromatography over silica gel
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated
  13. customThe residue is crystallized from 17.5 parts of petroleumether

Sources & evidence

ORD record
ord-6f0b50cbd7bd494d8dbc29f241df89df
Source dataset
uspto-grants-1981_01
Patent number
US04246429

Reaction notes

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