Benzaldehyde → (4-(Trifluoromethylthio)benzyl)malononitrile

HRID 749607Notes

Reaction equation

HRID 749607 reaction equation
[F:1][C:2]([F:17])([F:16])[S:3][C:4]1[CH:15]=[CH:14][C:7]([CH:8]=[C:9]([C:12]#[N:13])[C:10]#[N:11])=[CH:6][CH:5]=1.C(=O)C1C=CC=CC=1.C1(N)C=CC=CC=1N>C(O)C>[F:16][C:2]([F:1])([F:17])[S:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]([C:12]#[N:13])[C:10]#[N:11])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 7243O-PhenylenediamineHCID 222349754-(Trifluoromethylthio)benzylidenemalononitrile

Product 1

HCID 22234991(4-(Trifluoromethylthio)benzyl)malononitrileYield 77.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Then, 8.00 g of (4-(trifluoromethylthio)benzylidene)malononitrile and 3.35 g of benzaldehyde were dissolved in 320 ml of ethanol, and while stirring at room temperature, 3.41 g of phenylenediamine was slowly added, and the mixture was stirred at room temperature for 5 hours. Then, the reaction mixture was concentrated, 300 ml of t-butyl methyl ether was added, and insoluble matters were filtered. The filtrate was concentrated and the resulting residue was subjected to silica gel chromatography to give 6.22 g of (4-(trifluoromethylthio)benzyl)malononitrile (the intermediate (14)).

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hours
  2. concentrationThen, the reaction mixture was concentrated
  3. addition300 ml of t-butyl methyl ether was added
  4. filtrationinsoluble matters were filtered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9fb9eccb93004b279213118abb35b9b5
Source dataset
uspto-grants-2008_07
Patent number
US07402691B2

Reaction notes

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