Diethyl Malonate → 2-(3-chlorophenyl)-4,6-(1H,5H)-pyrimidinedione

HRID 1578964Notes

Reaction equation

HRID 1578964 reaction equation
[Na].Cl.[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH2:9])=[NH:8].[C:13](OCC)(=[O:20])[CH2:14][C:15](OCC)=[O:16]>C(O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:7]2[NH:9][C:13](=[O:20])[CH2:14][C:15](=[O:16])[N:8]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 5360545SodiumHCID 131653343-Chlorobenzene-1-carboximidamide hydrochloride

Product 1

HCID 215574062-(3-chlorophenyl)-4,6-(1H,5H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 56.4 g. of sodium metal in one liter of absolute ethanol there is added 156 g. of m-chlorobenzamidine hydrochloride followed by the dropwise addition of 144 g. of diethyl malonate over a fifteen minutes period. The reaction mixture is heated under reflux for three 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 (123 g., m.p. 254°-256°C.) is recrystallized from aqueous N,N-dimethylformamide to yield 2-(3-chlorophenyl)-4,6-(1H,5H)-pyrimidinedione, m.p. 256°-257°C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for three 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 the product (123 g., m.p. 254°-256°C.)
  9. customis recrystallized from aqueous N,N-dimethylformamide

Sources & evidence

ORD record
ord-a2f35bbb516d4d23893c33747046e1ee
Source dataset
uspto-grants-1976_02
Patent number
US03940395

Reaction notes

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