Diethyl Malonate → HCID 21557423, compound

HRID 1578966Notes

Reaction equation

HRID 1578966 reaction equation
[Na].Cl.[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[NH:9])=[CH:6][CH:5]=1.[C:13](OCC)(=[O:20])[CH2:14][C:15](OCC)=[O:16]>C(O)C>[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]2[NH:10][C:13](=[O:20])[CH2:14][C:15](=[O:16])[N:9]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 2034364-Chlorobenzene-1-carboximidamide hydrochlorideHCID 5360545Sodium

Product 1

HCID 21557423HCID 21557423, compound

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 p-chlorobenzamidine hydrochloride followed by the dropwise addition of 144 g. of diethyl malonate over a thirty minutes period. The reaction mixture is heated under reflux for five hours. The solution is filtered and the filter cake is 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 precipitates which is removed by filtration. Washing this material several times with water affords 2-(4-chlorophenyl)-4,6-(1H,5H)-pyrimidinedione.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for five hours
  3. filtrationThe solution is filtered
  4. dissolutionthe filter cake is 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 precipitates which
  8. customis removed by filtration
  9. washWashing this material several times with water

Sources & evidence

ORD record
ord-1be66ef311034179bcb8a80946c14b15
Source dataset
uspto-grants-1976_02
Patent number
US03940395

Reaction notes

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