Malononitrile → (1-Ethoxyethylidene)malononitrile

HRID 243316

Reaction equation

HRID 243316 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[C:6]([CH3:16])(OCC)(OCC)[O:7][CH2:8][CH3:9]>CC(O)=O>[CH2:6]([O:7][C:8](=[C:2]([C:1]#[N:5])[C:3]#[N:4])[CH3:9])[CH3:16]

Participants

4

Reactant 2

HCID 8010MalononitrileHCID 66221Triethyl orthoacetate

Product 1

HCID 79450(1-Ethoxyethylidene)malononitrileYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of malononitrile (5.0 g, 76 mmol), (EtO)3CCH3 (14.8 g, 91 mmol) and CH3COOH (1 mL) was stirred at 80° C. for 45 min. Then the mixture was cooled to room temperature and filtered to give 2-(1-ethoxy-ethylidene)-malononitrile (8.9 g, yield 86%) as a yellow solid.

Workup

  1. temperatureThen the mixture was cooled to room temperature
  2. filtrationfiltered

Sources & evidence

ORD record
ord-d1ed5381a1de43f9a4367b9d791ffd75
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Linked notes

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