Dimethylformamide dimethyl acetal → 2-[3-(Dimethylamino)-1-methoxy-2-propenylidene]malononitrile

HRID 2361738Notes

Reaction equation

HRID 2361738 reaction equation
[CH2:1]([O:3][C:4](=[C:6]([C:9]#[N:10])[C:7]#[N:8])[CH3:5])C.CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>CO>[CH3:13][N:14]([CH3:16])[CH:15]=[CH:5][C:4](=[C:6]([C:9]#[N:10])[C:7]#[N:8])[O:3][CH3:1]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 79450(1-Ethoxyethylidene)malononitrile

Product 1

HCID 27867762-[3-(Dimethylamino)-1-methoxy-2-propenylidene]malononitrileYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of D1 (34 g, 250 mmol) in MeOH (300 ml) was added N,N-dimethylformamide dimethyl acetal (44.68 g, 375 mmol). The reaction mixture was heated at reflux for 2 h. The mixture was then cooled to room temperature and a dark red solid precipitated upon cooling. The solid was filtered off, washed with cold methanol and dried in vacuo to yield compound D2 (16.2 g, 38%) as a red solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. customa dark red solid precipitated
  4. temperatureupon cooling
  5. filtrationThe solid was filtered off
  6. washwashed with cold methanol
  7. customdried in vacuo

Sources & evidence

ORD record
ord-95d36c51b9a74d98913bcf075158931b
Source dataset
uspto-grants-2014_04
Patent number
US08691813B2

Reaction notes

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