Sodium Chloride → 4-(Trifluoromethylthio)benzylidenemalononitrile

HRID 749606Notes

Reaction equation

HRID 749606 reaction equation
[F:1][C:2]([F:13])([F:12])[S:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.[C:14](#[N:18])[CH2:15][C:16]#[N:17].[Cl-].[Na+]>C(O)C.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>[F:1][C:2]([F:13])([F:12])[S:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[C:15]([C:14]#[N:18])[C:16]#[N:17])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 8010MalononitrileHCID 27778464-[(Trifluoromethyl)sulfanyl]benzaldehyde

Product 1

HCID 222349754-(Trifluoromethylthio)benzylidenemalononitrileYield 93.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 66854Benzyltrimethylammonium hydroxideSolvent

Procedure

First, 10.0 g of 4-(trifluoromethylthio)benzaldehyde and 2.92 g of malononitrile were dissolved in 50 ml of 70% (w/w) aqueous ethanol, to which a catalytic amount of benzyltrimethylammonium hydroxide was added, and the mixture was stirred at room temperature overnight. Then, a saturated aqueous sodium chloride solution was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was recrystallized with a solvent system consisting of t-butyl methyl ether and hexane to give 10.5 g of (4-(trifluoromethylthio)benzylidene)malononitrile.

Workup

  1. additionwas added
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized with a solvent system

Sources & evidence

ORD record
ord-87e2f05878ee4209af1c0bb1c5c4eacb
Source dataset
uspto-grants-2008_07
Patent number
US07402691B2

Reaction notes

Loading…