Diethyl (ethoxymethylene)malonate → HCID 67954353, compound

HRID 1846396Notes

Reaction equation

HRID 1846396 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[NH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:18][CH:19]=[C:20]([C:26](OCC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])C>C(O)C>[O:18]=[C:19]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[N:9][CH:26]=[C:20]1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 178511982HCID 178511982, compound2×

Product 1

HCID 67954353HCID 67954353, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
160 °C

Procedure

A suspension of the N-phenyl-3-pyridinecarboximidamide (i.e. the product from Example 7, Step A) (36.5 g, 185 mmol) in diethyl ethoxymethylenemalonate (60 g, 280 mmol) was heated to 160° C. for 8 h. Ethanol formed in the reaction was collected using a distillation head attached to the flask containing the heated reaction mixture. The reaction mixture was then cooled to ambient temperature when the formation of a solid was observed. A mixture of diethyl ether/petroleum ether (8:2) was added to the reaction mixture was filtered. The collected solid was washed with additional ether/petroleum ether (4:1) followed by n-chlorobutane/petroleum ether (1:1) to obtain 51 g of the title compound as a light brown powder.

Workup

  1. customwas collected
  2. additioncontaining
  3. customthe heated reaction mixture
  4. temperatureThe reaction mixture was then cooled to ambient temperature when the formation of a solid
  5. additionwas added to the reaction mixture
  6. filtrationwas filtered
  7. washThe collected solid was washed with additional ether/petroleum ether (4:1)

Sources & evidence

ORD record
ord-2708436d5662448399ecdc37279d2e5d
Source dataset
uspto-grants-2015_02
Patent number
US08952024B2

Reaction notes

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