Ethanol → 6-(3,4-dimethoxyphenyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione

HRID 65143

Reaktionsgleichung

Reaktionsgleichung von HRID 65143
[C:1]([CH2:13][C:14]([O:16]CC)=O)(=O)[C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1.[CH3:19][NH:20][C:21]([NH:23][CH3:24])=[O:22].C(O)C>Cl.O>[CH3:6][O:5][C:4]1[CH:3]=[C:2]([C:1]2[N:23]([CH3:24])[C:21](=[O:22])[N:20]([CH3:19])[C:14](=[O:16])[CH:13]=2)[CH:11]=[CH:10][C:7]=1[O:8][CH3:9]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 7293N,N'-DimethylureaHCID 2758465Ethyl 3,4-dimethoxybenzoylacetate

Produkt 1

HCID 140964656-(3,4-dimethoxyphenyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedioneAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysator2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a mixture of ethyl veratroylacetate (10 g) and N,N'-dimethylurea (3.84 g) were added conc. hydrochloric acid (1 drop) and ethanol (1 ml). The mixture was heated at 120° C. for 3.5 hours under reduced pressure. To the residue was added another conc. hydrochloric acid (2 drops) and the mixture was heated again at 120° C. for 4 hours under reduced pressure. To the reaction mixture was added water and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with a mixture of isopropyl ether and ethyl acetate to give 6-(3,4-dimethoxyphenyl)-1,3-dimethyl-2,4(1H,3H)pyrimidinedione (7.60 g).

Aufarbeitung

  1. temperaturethe mixture was heated again at 120° C. for 4 hours under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with a mixture of isopropyl ether and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-46819ab8a80f48119baf7d619bb8feff
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04612376

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