Hydrochloric Acid → HCID 13562808, compound

HRID 979143Notes

Reaction equation

HRID 979143 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[NH:11])[CH:6]=[CH:7][CH:8]=1.C(N([CH:20]([C:26]([O:28]CC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])CC)C.[C:31](=O)([O-])[O-].[K+].[K+].Cl>O.C(O)C>[O:28]=[C:26]1[NH:12][C:10]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:4]=2)=[N:11][CH:31]=[C:20]1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 292519Diethyl (diethylamino)propanedioateHCID 178512485HCID 178512485, compound

Product 1

HCID 13562808HCID 13562808, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of N-(3-trifluoromethylphenyl)guanidine (10 g), diethyl N,N-diethylaminomalonate (11.8 g) and potassium carbonate (13.4 g) in water (100 ml) and ethanol (100 ml) is refluxed with stirring for 7 hours. After cooling, the mixture is acidified to pH 3 with 10% aqueous HCl. The precipitate is collected by filtration, washed with water and recrystallized from a mixture of DMF and water to give ethyl 1,6-dihydro-6-oxo-2-(3-trifluoromethylanilino)-5-pyrimidinecarboxylate (13.4 g). M.p. 229°-231° C.

Workup

  1. temperatureis refluxed
  2. temperatureAfter cooling
  3. filtrationThe precipitate is collected by filtration
  4. washwashed with water
  5. customrecrystallized from a mixture of DMF and water

Sources & evidence

ORD record
ord-e9e9c3229a734388b30a4bc87dedb994
Source dataset
uspto-grants-1987_05
Patent number
US04666915

Reaction notes

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