Diethyl Malonate → HCID 21557410, compound

HRID 1578962Notes

Reaction equation

HRID 1578962 reaction equation
[Na].Cl.[C:3]1([CH3:12])[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([NH2:11])=[NH:10])[CH:4]=1.[C:13](OCC)(=[O:20])[CH2:14][C:15](OCC)=[O:16]>C(O)C>[C:3]1([CH3:12])[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[NH:10][C:13](=[O:20])[CH2:14][C:15](=[O:16])[N:11]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 28007013-methylbenzenecarboximidamide HydrochlorideHCID 5360545Sodium

Product 1

HCID 21557410HCID 21557410, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 35.8 g. of sodium metal in one liter of absolute ethanol, there is added 88.5 g. of m-toluamidine hydrochloride followed by the dropwise addition of 91.5 g. of diethyl malonate over a fifteen minutes period. The reaction mixture is heated under reflux for four hours. The solution is filtered and the filter cake dissolved in water. The ethanol filtrate is evaporated to dryness and the solid residue added to the water solution. Upon acidification of the aqueous solution to pH2 with concentrated hydrochloric acid, a solid separates which is removed by filtration. After washing this material several times with water, the product is recrystallized from aqueous N,N-dimethylformamide to afford 2-(3-tolyl)-4,6-(1H,5H)-pyrimidinedione, m.p. 247.5°c.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for four hours
  3. filtrationThe solution is filtered
  4. dissolutionthe filter cake dissolved in water
  5. customThe ethanol filtrate is evaporated to dryness
  6. additionthe solid residue added to the water solution
  7. customUpon acidification of the aqueous solution to pH2 with concentrated hydrochloric acid, a solid separates which is removed by filtration
  8. washAfter washing this material several times with water
  9. customthe product is recrystallized from aqueous N,N-dimethylformamide

Sources & evidence

ORD record
ord-94aa56830731447c9fb1093ef2b23d0a
Source dataset
uspto-grants-1976_02
Patent number
US03940395

Reaction notes

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