Malononitrile → 2-(1-Ethoxypropylidene)malononitrile

HRID 1990068Notes

Reaction equation

HRID 1990068 reaction equation
[C:1](OCC)(OCC)([O:4][CH2:5][CH3:6])[CH2:2][CH3:3].[C:13](#[N:17])[CH2:14][C:15]#[N:16]>>[CH2:5]([O:4][C:1](=[C:14]([C:13]#[N:17])[C:15]#[N:16])[CH2:2][CH3:3])[CH3:6]

Participants

3

Reactant 2

HCID 8010MalononitrileHCID 66995Ethyl orthopropionate

Product 1

HCID 2314702-(1-Ethoxypropylidene)malononitrile

Procedure

Heat a mixture of triethyl orthopropionate (446 g, 2.53 mol) and malononitrile (163.9 g, 2.48 mol) at reflux under nitrogen for 1.5 h. Cool the mixture and stir overnight. Distill the dark mixture under vacuum (10-15 torr, 135-142° C.) to afford the title compound as a pale yellow oil: 1H NMR (CDCl3) δ 4.40 (q, J=7.0, 2H), 2.63, (q, J=7.7, 2H), 1.41 (t, J=7, 3H), 1.23 (t, J=7.7, 3H); 13C NMR (CDCl3) 189.7, 113.3, 111.8, 68.3, 64.1, 25.5, 14.6, 11.3.

Workup

  1. temperatureHeat
  2. temperatureat reflux under nitrogen for 1.5 h
  3. temperatureCool the mixture
  4. distillationDistill the dark mixture under vacuum (10-15 torr, 135-142° C.)

Sources & evidence

ORD record
ord-6e378796b3de4f48be17591764b80e8d
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

Loading…