Acetonitrile → HCID 10798029, compound

HRID 132973Notes

Reaction equation

HRID 132973 reaction equation
Br[CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[C:5]([CH2:11]Br)[C:4]=1[CH3:13].[C-:14]#[N:15].[K+].C1OCCOCCOCCOCCOCCOC1.[C:35](#[N:37])C>>[C:14]([CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[C:5]([CH2:11][C:35]#[N:37])[C:4]=1[CH3:13])#[N:15]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 43867201,3-bis(bromomethyl)-2,4,6-trimethylbenzene

Product 1

HCID 10798029HCID 10798029, compound

Procedure

In the above reaction scheme, 1,3-bis(bromomethyl)-2,4,6-trimethylbenzene is reacted with KCN in the presence of a phase transfer catalyst, commonly known as 18-crown-6, (from Aldrich) in acetonitrile. The two-phase system is heated to reflux with vigorous stirring. After two hours, the reaction mixture is cooled, filtered, and evaporated to approximately one-third volume. Distilled water is added, and the mixture is extracted with dichloromethane. The dichloromethane solution is dried over sodium sulfate and filtered, and the solvent evaporated under reduced pressure to obtain 1,3-di(cyanomethyl)-2,4,6-trimethylbenzene.

Workup

  1. temperatureThe two-phase system is heated
  2. temperatureto reflux with vigorous stirring
  3. temperaturethe reaction mixture is cooled
  4. filtrationfiltered
  5. customevaporated to approximately one-third volume
  6. additionDistilled water is added
  7. extractionthe mixture is extracted with dichloromethane
  8. dry with materialThe dichloromethane solution is dried over sodium sulfate
  9. filtrationfiltered
  10. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-0131fecb2d8e4e24b4d386ba4c2326ce
Source dataset
uspto-grants-2008_06
Patent number
US07390430B2

Reaction notes

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