Malononitrile → 2-(2,5-Dichloro-benzylidene)-malononitrile

HRID 1094047

Reaction equation

HRID 1094047 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH:4]=O.[C:11](#[N:15])[CH2:12][C:13]#[N:14].[OH-].[K+].O>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH:4]=[C:12]([C:11]#[N:15])[C:13]#[N:14]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 807022,5-DichlorobenzaldehydeHCID 23719240Potassium hydroxide monohydrate

Product 1

HCID 595516612-(2,5-Dichloro-benzylidene)-malononitrileYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,5-dichlorbenzaldehyde (4.0 g, 0.0228 mole) in ethanol (6 ml) was added malononitrile (1.52 g, 0.0228 mole), followed by 100 μl, of 10% KOH/H2O. The mixture was stirred at room temperature for 2 hrs and then filtered to give 2-(2,5-Dichloro-benzylidene)-malononitrile (8a, 4.82 g) in 95% yield. 1H-NMR (400 MHz, d6-DMSO): δ ppm 8.66 (s, 1H), 8.07 (d, J=2.0 Hz, 1H), 7.74 (s, 1H), 7.74 (s, 1H). MS [m+H] calc'd for C10H4Cl2N2, 223.0, 224.8; found 223.0, 224.8.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-230051c2541c41b3838d0fffed178f44
Source dataset
uspto-grants-2012_03
Patent number
US08133898B2

Linked notes

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