Water → 2-(6-Chloropyridin-3-yl)acetonitrile

HRID 1089439Notes

Reaction equation

HRID 1089439 reaction equation
[C-:1]#[N:2].[Na+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11]Cl)=[CH:7][N:6]=1.O>CS(C)=O>[Cl:4][C:5]1[N:6]=[CH:7][C:8]([CH2:11][C:1]#[N:2])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 14751282-(6-Chloropyridin-3-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

25.6 g of sodium cyanide (0.522 mol) are dissolved in 123 g of dimethyl sulfoxide, the mixture is heated to 90° C. and 68.9 g (0.43 mol) of 2-chloro-5-chloromethylpyridine are introduced in portions. During this, the temperature rises to 130° C. The mixture is allowed to cool to room temperature, poured into water and extracted using ether. The solvent is removed and the crude product is distilled at 1.0 mbar (130°-135° C.). M.p.: 80° C. Yield: 41.1 g (63% of theory).

Workup

  1. customrises to 130° C
  2. temperatureto cool to room temperature
  3. extractionextracted
  4. customThe solvent is removed
  5. distillationthe crude product is distilled at 1.0 mbar (130°-135° C.)

Sources & evidence

ORD record
ord-5b450b66a6ac46758fde4ef1f15d0cbf
Source dataset
uspto-grants-1990_10
Patent number
US04966902

Reaction notes

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