Benzyl Isothiocyanate → HCID 54355338, compound

HRID 1290721Notes

Reaction equation

HRID 1290721 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[H-].[Na+].[CH2:8]([N:15]=[C:16]=[S:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:18]I>CN(C=O)C.O>[CH3:18][S:17][CH:16]([NH:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:2]([C:1]#[N:5])[C:3]#[N:4]

Participants

7

Reactant 4

HCID 2346Benzyl IsothiocyanateHCID 6328Methyl iodideHCID 8010MalononitrileHCID 24758Sodium hydride

Product 1

HCID 54355338HCID 54355338, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of malononitrile (1.21 g, 18.3 mmol) in DMF (40 ml) was added under ice-cooling sodium hydride (0.77 g, 19.2 mmol). After stirring for one hour, benzyl isothiocyanate (2.73 g, 18.3 mmol) was added dropwise. After stirring under ice-cooling for 1.5 hours, methyl iodide (2.60 g, 18.3 mmol) was added dropwise. After stirring at room temperature for 15 hours, water (400 ml) was added to the reaction mixture, which was then extracted with ethyl acetate (100 ml×2). The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a yellow oily substance (2.94 g) from the fraction from hexane-ethyl acetate (2/1). Yield=70%.

Workup

  1. stirringAfter stirring under ice-
  2. temperaturecooling for 1.5 hours
  3. stirringAfter stirring at room temperature for 15 hours
  4. extractionwas then extracted with ethyl acetate (100 ml×2)
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-67ab4d2350e247a1be7158d1939fd4a9
Source dataset
uspto-grants-1998_05
Patent number
US05753654

Reaction notes

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