Benzaldehyde → HCID 20296018, compound

HRID 1389930

Reaction equation

HRID 1389930 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([Cl:17])=[CH:12][C:11]=1[NH2:18].[C-:19]#[N:20].[K+]>[Cl-].[Zn+2].[Cl-].O>[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([Cl:17])=[CH:12][C:11]=1[NH:18][CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:19]#[N:20]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 9032Potassium CyanideHCID 124872,4,5-Trichloroaniline

Product 1

HCID 20296018HCID 20296018, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred mixture of 53 parts of benzaldehyde in 820 parts of water are added successively 78.6 parts of 2,4,5-trichlorobenzenamine, 81.8 parts of zinc chloride and 32.6 parts of potassium cyanide and the whole is stirred for 18 hours at 50° C. The reaction mixture is cooled to room temperature. The precipitated product is filtered off, triturated in 1000 parts of water, filtered off again and dissolved in 750 parts of trichloromethane. The solution is washed twice with water, dried, filtered and evaporated. The solid residue is triturated in petroleum ether, filtered off again and dried, yielding 83.1 parts of α-[(2,4,5-trichlorophenyl)amino]benzeneacetonitrile; mp. 123.7° C.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationThe precipitated product is filtered off
  3. customtriturated in 1000 parts of water
  4. filtrationfiltered off again
  5. dissolutiondissolved in 750 parts of trichloromethane
  6. washThe solution is washed twice with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe solid residue is triturated in petroleum ether
  11. filtrationfiltered off again
  12. customdried

Sources & evidence

ORD record
ord-d1698bafec5a4e2fb43185c9e8bd4d09
Source dataset
uspto-grants-1981_01
Patent number
US04246429

Linked notes

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