Crotyl chloride → HCID 54222982, compound

HRID 1605685Notes

Reaction equation

HRID 1605685 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]#[N:9].[H-].[Na+].Cl[CH2:13][CH:14]=[CH:15][CH3:16]>CS(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([CH2:13][CH:14]=[CH:15][CH3:16])[C:8]#[N:9]

Participants

5

Reactant 3

HCID 11589Crotyl chlorideHCID 24758Sodium hydrideHCID 75959Pyridine-2-acetonitrile

Product 1

HCID 54222982HCID 54222982, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 5.9 g. of 2-pyridylacetonitrile in 15 ml. of dimethylsulfoxide is added to a suspension of 1.2 g. of sodium hydride in 25 ml. of dimethylsulfoxide with stirring. The mixture is heated on a stream bath for 2 hours, then cooled to room temperature. 1-Chloro-2-butene (4.5 g.) is added dropwise with stirring. The mixture is heated on a steam bath, with stirring, for 10 hours, then most of the solvent is removed in vacuo. Water is added to the residue, then 100 ml. of ether is added. The ethereal solution is separated from the aqueous layer and rinsed several times with water, then dried, concentrated and distilled to give 2-(2-pyridyl)-4-hexenenitrile.

Workup

  1. temperatureThe mixture is heated on a stream bath for 2 hours
  2. temperatureThe mixture is heated on a steam bath
  3. stirringwith stirring, for 10 hours
  4. custommost of the solvent is removed in vacuo
  5. additionWater is added to the residue
  6. additionof ether is added
  7. customThe ethereal solution is separated from the aqueous layer
  8. washrinsed several times with water
  9. customdried
  10. concentrationconcentrated
  11. distillationdistilled

Sources & evidence

ORD record
ord-f18be553f66e435f8930dc4bfedd5bf8
Source dataset
uspto-grants-1976_04
Patent number
US03950522

Reaction notes

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