Sulfur Dioxide → HCID 13497266, compound

HRID 437706Notes

Reaction equation

HRID 437706 reaction equation
[C:1]([C:3](=[C:6](O)[C:7]([CH3:10])([CH3:9])[CH3:8])[C:4]#[N:5])#[N:2].P(Cl)(Cl)(Cl)(Cl)[Cl:13].S(=O)=O>C(Cl)Cl>[Cl:13][C:6]([C:7]([CH3:10])([CH3:9])[CH3:8])=[C:3]([C:4]#[N:5])[C:1]#[N:2]

Participants

5

Reactant 3

HCID 1119Sulfur DioxideHCID 24819Phosphorus pentachlorideHCID 21426743(1-Hydroxy-2,2-dimethylpropylidene)propanedinitrile

Product 1

HCID 13497266HCID 13497266, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 69.6 g of 2-cyano-3-hydroxy-4,4-dimethyl- 2-pentenenitrile in 600 ml of methylene chloride was added in small portions 104.1 g of phosphorus pentachloride. The mixture was stirred for 22 hours at room temperature. Sulfur dioxide was passed through the mixture for 20 minutes and the mixture stirred for an additional hour. The mixture was concentrated and poured into 500 ml of ice. After stirring for 1 hour, the cold mixture was filtered, the solid was washed with cold water and dried in a vacuum oven at room temperature for 60 hours to give 68.8 g of 3-chloro-2-cyano-4,4-dimethyl- 2-pentenenitrile, mp 52°-53°.

Workup

  1. stirringthe mixture stirred for an additional hour
  2. concentrationThe mixture was concentrated
  3. additionpoured into 500 ml of ice
  4. stirringAfter stirring for 1 hour
  5. filtrationthe cold mixture was filtered
  6. washthe solid was washed with cold water
  7. customdried in a vacuum oven at room temperature for 60 hours

Sources & evidence

ORD record
ord-f38ad10c1c4349049e9e061840a41450
Source dataset
uspto-grants-1977_06
Patent number
US04032322

Reaction notes

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