Benzamidine → HCID 21709567, compound

HRID 1578961Notes

Reaction equation

HRID 1578961 reaction equation
[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5]CC)=O.[C:12]([NH2:20])(=[NH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Na]>C(O)C>[C:13]1([C:12]2[NH:20][C:3](=[O:5])[CH2:2][C:1](=[O:9])[N:19]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 2332BenzamidineHCID 7761Diethyl MalonateHCID 5360545Sodium

Product 1

HCID 21709567HCID 21709567, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Wherein R1, R2 and R3 are defined as above. The cyclization reaction between the commercially available diethyl malonate and an appropriate benzamidine is effected by refluxing a substantially equimolar mixture of these reactants in a reaction-inert solvent, such as ethanol, in the presence of sodium metal for a period of about two to about five hours. After the reaction is complete, the reaction mixture is filtered, the filter cake dissolved in water and precipitated by acidification to afford a 2-phenyl-4,6-(1H,5H)-pyrimidinedione (I).

Workup

  1. temperatureby refluxing
  2. additiona substantially equimolar mixture of these reactants in a reaction-inert solvent
  3. filtrationthe reaction mixture is filtered
  4. dissolutionthe filter cake dissolved in water
  5. customprecipitated by acidification

Sources & evidence

ORD record
ord-081e9d5efa614e399d72d81f927e15ba
Source dataset
uspto-grants-1976_02
Patent number
US03940395

Reaction notes

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