Acetic Acid → Ethyl 1,6-dihydro-6-oxo-2-(2-propoxyphenyl)pyrimidine-5-carboxylate

HRID 437432

Reaktionsgleichung

Reaktionsgleichung von HRID 437432
COS(O)(=O)=O.[CH2:7]([O:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([NH2:15])=[NH:14])[CH2:8][CH3:9].C(=O)([O-])[O-].[K+].[K+].C([O:28][CH:29]=[C:30]([C:36](OCC)=O)[C:31]([O:33][CH2:34][CH3:35])=[O:32])C.C(O)(=O)C>C(O)C>[O:28]=[C:29]1[NH:15][C:13]([C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[O:10][CH2:7][CH2:8][CH3:9])=[N:14][CH:36]=[C:30]1[C:31]([O:33][CH2:34][CH3:35])=[O:32]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 11430Potassium CarbonateHCID 86734867n-Propoxybenzamidine methyl sulfate

Produkt 1

HCID 12535801Ethyl 1,6-dihydro-6-oxo-2-(2-propoxyphenyl)pyrimidine-5-carboxylateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-n-propoxybenzamidine methyl sulfate 7.4 g., 0.0255 mole), potassium carbonate (3.53 g., 0.025 mole), and diethyl ethoxymethylenemalonate (5.99 g., 0.0277 mole) in ethanol (80 ml.) was heated under reflux with stirring for 17 hours. The cooled mixture was added to ice-water (160 ml.) which was then acidified with glacial acetic acid. The precipitate was collected by filtration, washed with water, and dried to give the title compound (6.55 g., 89%), m.p. 106°-107°.

Aufarbeitung

  1. temperatureunder reflux
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7026d10e25c44287b5b29e96cc6ed433
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04031093

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