Sodium Hydroxide → alpha-(3,4-Dichlorophenyl)-alpha-(2,6-dichloro-4-nitrophenyl)acetonitrile

HRID 321983Notes

Reaction equation

HRID 321983 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[CH2:5][C:6]#[N:7].Br[C:13]1[C:18]([Cl:19])=[CH:17][C:16]([N+:20]([O-:22])=[O:21])=[CH:15][C:14]=1[Cl:23].[OH-].[Na+]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]([C:13]2[C:14]([Cl:23])=[CH:15][C:16]([N+:20]([O-:22])=[O:21])=[CH:17][C:18]=2[Cl:19])[C:6]#[N:7])[CH:8]=[CH:9][C:10]=1[Cl:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76690(3,4-Dichlorophenyl)acetonitrileHCID 99933122-Bromo-1,3-dichloro-5-nitrobenzene

Product 1

HCID 22008581alpha-(3,4-Dichlorophenyl)-alpha-(2,6-dichloro-4-nitrophenyl)acetonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To 150 ml of 20% hydrous DMSO were added 6.15 g of 3,4-dichlorobenzyl cyanide, 8.13 g of 4-bromo-3,5-dichloronitrobenzene and 1.50 g of sodium hydroxide. The reaction was allowed to proceed for one hour at temperatures ranging from 60 to 70° C. After completion of the reaction, DMSO was removed, and the residue was dissolved in 50 ml of toluene. The solution was washed with water, dried and concentrated. To the concentrate was added ethyl alcohol to cause crystallization to afford the titled compound in a yield of 67%, m.p.171-172° C.

Workup

  1. customranging from 60 to 70° C
  2. customwas removed
  3. dissolutionthe residue was dissolved in 50 ml of toluene
  4. washThe solution was washed with water
  5. customdried
  6. concentrationconcentrated
  7. additionTo the concentrate was added ethyl alcohol
  8. customcrystallization

Sources & evidence

ORD record
ord-d5d57baf1dee47728c1cadcd99808389
Source dataset
uspto-grants-2001_04
Patent number
US06211178B1

Reaction notes

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