3,4-Dichlorobenzyl chloride → HCID 21320353, compound

HRID 262195Notes

Reaction equation

HRID 262195 reaction equation
CC([O-])(C)C.[K+].[F:7][C:8]([F:27])([F:26])[C:9]1[CH:10]=[C:11]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[NH:12][CH:13]=[C:14]([C:17]#[N:18])[C:15]#[N:16].[Cl:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][C:36]=1[Cl:37])[CH2:32]Cl>CS(C)=O>[C:15]([C:14]([C:17]#[N:18])=[CH:13][N:12]([CH2:32][C:31]1[CH:34]=[CH:35][C:36]([Cl:37])=[C:29]([Cl:28])[CH:30]=1)[C:11]1[CH:10]=[C:9]([C:8]([F:26])([F:27])[F:7])[CH:21]=[C:20]([C:22]([F:25])([F:23])[F:24])[CH:19]=1)#[N:16]

Participants

5

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 2797077Propanedinitrile, [[[3,5-bis(trifluoromethyl)phenyl]amino]methylene]-HCID 23665647Potassium tert-butoxide

Product 1

HCID 21320353HCID 21320353, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

With stirring, 16.8 g of potassium tert-butylate are added by small amounts to a solution of 45.7 g of 3,5-bis-trifluoromethyl-N-(2,2-dicyanovinyl)-aniline in 200 ml of dimethyl sulphoxide. The solution is kept for 4 hours at 40° C. With further stirring, 20.8 ml of 3,4-dichlorobenzyl chloride in 20 ml of dimethyl sulphoxide are added dropwise and the reaction mixture is then stirred for 12 hours at 40° C. The mixture is then poured onto 2 liters of ice and the precipitated product is extracted with chloroform. The chloroform solution is washed with water, dried over sodium sulphate and the chloroform is distilled off. The crude product is chromatographed over a silica gel column with methyl acetate/hexane (1:3 v/v) as eluant, yielding 15 g of the desired product in the form of yellow crystals with a melting point of 102°-103° C.

Workup

  1. stirringthe reaction mixture is then stirred for 12 hours at 40° C
  2. extractionthe precipitated product is extracted with chloroform
  3. washThe chloroform solution is washed with water
  4. dry with materialdried over sodium sulphate
  5. distillationthe chloroform is distilled off
  6. customThe crude product is chromatographed over a silica gel column with methyl acetate/hexane (1:3 v/v) as eluant

Sources & evidence

ORD record
ord-225acab61f51469e8127b050b0112051
Source dataset
uspto-grants-1979_05
Patent number
US04153723

Reaction notes

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