Hydrochloric Acid → (3,4-Dichlorobenzyl)malononitrile

HRID 749604Notes

Reaction equation

HRID 749604 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[Cl:14])[CH:5]=[C:6]([C:9]#[N:10])[C:7]#[N:8].[BH4-].[Na+].Cl>O1CCCC1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[Cl:14])[CH2:5][CH:6]([C:7]#[N:8])[C:9]#[N:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 219328(3,4-Dichlorobenzylidene)malononitrileHCID 4311764Sodium borohydride

Product 1

HCID 12194483(3,4-Dichlorobenzyl)malononitrileYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

First, 4.46 g of (3,4-dichlorobenzylidene)malononitrile was dissolved in 20 ml of tetrahydrofuran, and while stirring at room temperature, a suspension of 0.19 g of sodium borohydride in 5 ml of ethanol was added dropwise, followed by stirring at room temperature for 30 minutes. Then, 10% hydrochloride acid was added and the mixture was extracted with diethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 3.15 g of (3,4-dichlorobenzyl)malononitrile (the intermediate (12)).

Workup

  1. additionwas added dropwise
  2. stirringby stirring at room temperature for 30 minutes
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe organic layer was successively washed with 10% hydrochloric acid
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f71aa01e8e34f329b623e084015c4cf
Source dataset
uspto-grants-2008_07
Patent number
US07402691B2

Reaction notes

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