Methyl iodide → Propanedinitrile, 2-[(methylamino)(methylthio)methylene]-

HRID 262163Notes

Reaction equation

HRID 262163 reaction equation
[H-].[Na+].[C:3](#[N:7])[CH2:4][C:5]#[N:6].[CH3:8][N:9]=[C:10]=[S:11].[CH3:12]I>CN(C)C=O>[C:5]([C:4]([C:3]#[N:7])=[C:10]([S:11][CH3:12])[NH:9][CH3:8])#[N:6]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8010MalononitrileHCID 11167Methyl isothiocyanateHCID 24758Sodium hydride

Product 1

HCID 3640288Propanedinitrile, 2-[(methylamino)(methylthio)methylene]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Sodium hydride (50% oil dispersion, 9.6 g) was added portionwise to a solution of malononitrile (13.21 g) in dry dimethylformamide (150 ml). The mixture was stirred at 0° for 10 minutes and then to it was added dropwise a solution of methyl isothiocyanate (14.62 g) in dimethylformamide, maintaining the reaction temperature below 40°. The dark red solution was stirred for 45 minutes and a solution of methyl iodide (28.4 g) in dimethylformamide (25 ml) was then added. The reaction mixture was stirred vigorously for 20 minutes and then poured on to crushed ice (500 ml). The crude product (26 g, m.p. 115°) was filtered off and taken up in hot ethanol ether (3:1, 600 ml). Filtration and cooling furnished 1,1-dicyano-2-methylthio-2-methylamino ethylene m.p. 119°-120°. Further recrystallisation from water gave a sample of m.p. 120°-121°.

Workup

  1. temperaturemaintaining the reaction temperature below 40°
  2. stirringThe dark red solution was stirred for 45 minutes
  3. stirringThe reaction mixture was stirred vigorously for 20 minutes
  4. additionpoured on
  5. filtrationThe crude product (26 g, m.p. 115°) was filtered off
  6. filtrationFiltration
  7. temperaturecooling

Sources & evidence

ORD record
ord-439a3a0b773140e4a988f519a697da89
Source dataset
uspto-grants-1979_05
Patent number
US04153704

Reaction notes

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