Diethyl Malonate → HCID 178482450, compound

HRID 1632900Notes

Reaction equation

HRID 1632900 reaction equation
[Cl-].C[NH3+].[C:4]([NH:6][C:7]([NH2:9])=[NH:8])#N.C[O-].[Na+].[C:13](OCC)(=[O:20])[CH2:14][C:15](OCC)=[O:16]>CO.O>[CH3:4][NH:6][C:7]1[N:9]=[C:15]([OH:16])[CH:14]=[C:13]([OH:20])[N:8]=1

Participants

7

Reactant 4

HCID 7761Diethyl MalonateHCID 11637Methanamine, hydrochloride (1:1)HCID 10942334Sodium MethoxideHCID 178418324HCID 178418324, compound

Product 1

HCID 178482450HCID 178482450, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
175 °C

Procedure

67.5 g (1 mole) of methylammonium chloride and 42 g (0.5 mole) of cyanoguanidine are heated to 175° C. to give a clear colourless melt. After onset of reaction, the heat of reaction causes the temperature of the reaction mixture to rise to 206° C. The batch is then stirred for 31/2 hours at 175° C., cooled to 80° C., diluted with 320 ml of methanol and then 172.3 g (0.97 mole) of a 30% solution of sodium methylate in methanol are added over 5 minutes. The resultant suspension is refluxed for 30 minutes and then 173 g (1.08 mole) of diethyl malonate are added over 5 minutes. This suspension is refluxed for another 6 hours and then diluted with 1.25 liters of water. The product is precipitated by acidifying the clear orange solution with glacial acetic acid to pH 4.5. The precipitate is isolated, washed with water and dried in vacuo over phosphorus pentoxide, affording 35.3 g (25% of theory) of 2-methylamino-4,6-dihydroxypyrimidine with a melting point of 290° C.

Workup

  1. customto give a clear colourless melt
  2. customAfter onset of reaction
  3. temperaturethe heat of reaction
  4. customto rise to 206° C
  5. temperaturecooled to 80° C.
  6. temperatureThis suspension is refluxed for another 6 hours
  7. customThe product is precipitated
  8. customThe precipitate is isolated
  9. washwashed with water
  10. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-43fa840be61d42f1937dbf4ebc664968
Source dataset
uspto-grants-1984_10
Patent number
US04478635

Reaction notes

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