Hydrazine hydrate (1:1) → HCID 178503599, compound

HRID 2202612Notes

Reaction equation

HRID 2202612 reaction equation
[CH3:1][S:2][C:3](SC)=[C:4]([C:7]#[N:8])[C:5]#[N:6].O.[NH2:12][NH2:13]>CCO>[NH2:8][C:7]1[C:4]([C:5]#[N:6])=[C:3]([S:2][CH3:1])[NH:13][N:12]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 992292-(Bis(methylsulfanyl)methylidene)propanedinitrile

Product 1

HCID 178503599HCID 178503599, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 2-(bis(methylthio)methylene)malononitrile (5.0 g, 29.37 mmol) in EtOH (20 mL) was added a solution of hydrazine hydrate (64% solution in water) (1.469 g, 45.82 mmol) in EtOH (10 mL) dropwise with stirring. The reaction mixture was stirred at room temperature for 1 hr and then at 70° C. overnight. After the reaction mixture was concentrated, the solid residual was trituated with EtOAc and hexanes. The resulting solid was filtered and dried to give compound I-12 (3.243 g, 71.7% yield, 94.7% purity) as a white powder.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hr
  2. customat 70° C.
  3. customovernight
  4. concentrationAfter the reaction mixture was concentrated
  5. filtrationThe resulting solid was filtered
  6. customdried
  7. customto give compound I-12 (3.243 g, 71.7% yield, 94.7% purity) as a white powder

Sources & evidence

ORD record
ord-d4600b4240da4134ae9439770304346b
Source dataset
uspto-grants-2016_06
Patent number
US09365556B2

Reaction notes

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