Methylamine → [1-(Methylamino)ethylidene]propanedinitrile

HRID 1865049Notes

Reaction equation

HRID 1865049 reaction equation
[CH3:1][NH2:2].C(O[C:6](=[C:8]([C:11]#[N:12])[C:9]#[N:10])[CH3:7])C>CCOCC>[CH3:1][NH:2][C:6](=[C:8]([C:11]#[N:12])[C:9]#[N:10])[CH3:7]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 79450(1-Ethoxyethylidene)malononitrile

Product 1

HCID 14027930[1-(Methylamino)ethylidene]propanedinitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add methylamine (1120 mL, 2.6 Eq.) to 2-(1-ethoxy-ethylidene)-malononitrile (115 g, 0.84 mol) in ether dropwise while stirring at room temperature under a nitrogen atmosphere. Stir at this temperature for 2 hours and then concentrate under reduced vacuum. Triturate the resulting solid in ethyl acetate (400 mL) and filter to produce 102 g of the title compound as a tan solid. Mass spectrum (m/e): 122.0 (M*+1): (Bruker 300)

Workup

  1. stirringStir at this temperature for 2 hours
  2. concentrationconcentrate under reduced vacuum
  3. customTriturate the resulting solid in ethyl acetate (400 mL)
  4. filtrationfilter

Sources & evidence

ORD record
ord-c425cce8b6bf490089ed307eea35c8a0
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

Loading…