Sodium Cyanide → Benzeneacetonitrile, 2,3-dichloro-

HRID 1800823Notes

Reaction equation

HRID 1800823 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[C-:11]#[N:12].[Na+]>CS(C)=O.O>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][C:11]#[N:12]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 76790Dichlorobenzyl chloride

Product 1

HCID 229020Benzeneacetonitrile, 2,3-dichloro-

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2,3-Dichlorobenzylchloride (5.0 g, 25.5 mmol) was dissolved in 100 ml DMSO. 9.2 g NaCN (188 mmol) were added and the mixture stirred at room temperature for 16 hours. The reaction mixture was diluted with water, and the product extracted with ether. The organic layers were washed with water (2×) and brine, then dried over magnesium sulfate, filtered and concentrated. The product was used as. Crude yield˜quantitative. An analytical sample was purified by column chromatography on silica, using a gradient from 10% to 75% dichloromethane in hexanes as eluent. The combined aqueous layers and wash liquids were treated with 100 ml bleach to oxidize the excess cyanide to less toxic materials.

Workup

  1. extractionthe product extracted with ether
  2. washThe organic layers were washed with water (2×) and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customAn analytical sample was purified by column chromatography on silica
  7. washThe combined aqueous layers and wash liquids
  8. additionwere treated with 100 ml bleach

Sources & evidence

ORD record
ord-95132224f2204bf5be33c7423de2b104
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

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