1,1-Dichloroethane → 6-Chloro-2-nitrobenzonitrile

HRID 894948Notes

Reaction equation

HRID 894948 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C-:12]#[N:13].[Na+].ClC(Cl)C>CN(C)C=O>[Cl:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([N+:9]([O-:11])=[O:10])[C:2]=1[C:12]#[N:13]

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 8929Sodium CyanideHCID 185552,3-Dichloronitrobenzene

Product 1

HCID 810536-Chloro-2-nitrobenzonitrileYield 78.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3-dichloronitrobenzene (19.2 g), cuprous chloride (2.4 g), anhydrous cupric sulfate (1.0 g), sodium cyanide (purity of 90%, 5.4 g) and dimethylformamide (3.0 g) were heated together to 190° C. and made to react for 3.5 hours at the temperature. After the reaction was over, 100 ml of dichloroethane were added to the reaction mixture and the mixture was filtered. After separating the filtrate, 100 ml of an aqueous 5% solution of ammonia were added to the filtrate and after well shaking the mixture, it was separated into layers. After distilling off dichloroethane from the organic layer and washing the residue with ethanol, 14.3 g of 2-chloro-6-nitrobenzonitrile was obtained as a pale yellow crystal. The yield was 78% theoretical.

Workup

  1. customto react for 3.5 hours at the temperature
  2. additionwere added to the reaction mixture
  3. filtrationthe mixture was filtered
  4. customAfter separating the filtrate, 100 ml of an aqueous 5% solution of ammonia
  5. additionwere added to the filtrate
  6. customwas separated into layers
  7. distillationAfter distilling off dichloroethane from the organic layer
  8. washwashing the residue with ethanol

Sources & evidence

ORD record
ord-d75071182b7d4916aa81c1b0e4dd01b7
Source dataset
uspto-grants-1981_08
Patent number
US04285883

Reaction notes

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