Malononitrile → 2-[(2,4,6-Trimethylphenyl)methylene]propanedinitrile

HRID 2420784Notes

Reaction equation

HRID 2420784 reaction equation
[C:1]1([CH3:11])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH:9]=O.[C:12](#[N:16])[CH2:13][C:14]#[N:15].N1CCCCC1>C(O)CCC>[C:1]1([CH3:11])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH:9]=[C:13]([C:12]#[N:16])[C:14]#[N:15]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8082PiperidineHCID 102542,4,6-Trimethylbenzaldehyde

Product 1

HCID 5930572-[(2,4,6-Trimethylphenyl)methylene]propanedinitrile

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
-20 °C

Procedure

In analogy to the methods described by M. Boehringer et al., WO 03/068748, a solution of 25 g (169 mmol) of mesitaldehyde (2,4,6-trimethylbenzaldehyde) and 13.5 g (204 mmol) of malononitrile in 70 mL of n-butanol was stirred at room temperature for 1 h and then treated dropwise with 0.4 mL of piperidine, resulting in a color change and precipitation. After 5 h, the mixture was cooled in a freezer (−20° C.) for 10 min and then filtered. The solid was washed three times with cold n-butanol and then dried to give the title compound as a white solid. LC-MS 197 (M+1). This material has been reported as being made by a similar procedure [A. M. Shestapalov et al., Chem. Heterocycl. Compd. (Engl. Transl. of Khim. Geterotsikl. Soedin.), 38, 1345 (2002)].

Workup

  1. customresulting in a color change and precipitation
  2. filtrationfiltered
  3. washThe solid was washed three times with cold n-butanol
  4. customdried

Sources & evidence

ORD record
ord-c6150e1f3657497787f95528fcff7680
Source dataset
uspto-grants-2011_06
Patent number
US07956061B2

Reaction notes

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