Diethyl Malonate → HCID 178418389, compound

HRID 1608783Notes

Reaction equation

HRID 1608783 reaction equation
[O-]CC.[Na+].[Na].[C:6]([O:14]CC)(=O)[CH2:7][C:8]([O:10]CC)=O.Cl.[C:18]([NH2:21])(=[NH:20])[CH3:19]>C(O)C>[OH:14][C:6]1[CH:7]=[C:8]([OH:10])[N:21]=[C:18]([CH3:19])[N:20]=1

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 67170Acetamidine monohydrochlorideHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 178418389HCID 178418389, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium ethoxide, prepared from sodium (36.2 g) and ethanol (1000 ml), diethyl malonate (114 ml) and acetamidine hydrochloride (71 g) were added at room temperature, and the mixture was stirred for 5 hours under reflux. After cooling to room temperature, the resulting solid was collected by filtration and washed with ethanol and then dissolved in water. The aqueous solution was acidified to pH Ca.2 with concentrated hydrochloric acid (Ca. 170 ml) under ice-cooling. The formed precipitate was separated by filtration and washed with water, ethanol and ether to give 153 g (81%) of the objective compound.

Workup

  1. additionwere added at room temperature
  2. temperatureunder reflux
  3. filtrationthe resulting solid was collected by filtration
  4. washwashed with ethanol
  5. dissolutiondissolved in water
  6. temperature2 with concentrated hydrochloric acid (Ca. 170 ml) under ice-cooling
  7. customThe formed precipitate was separated by filtration
  8. washwashed with water, ethanol and ether

Sources & evidence

ORD record
ord-b08984258b144cbf9e5291dc0fc80942
Source dataset
uspto-grants-1995_03
Patent number
US05397781

Reaction notes

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