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

HRID 2082726

Reaktionsgleichung

Reaktionsgleichung von HRID 2082726
[Na].COS(O)(=O)=O.[CH2:8]([O:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([NH2:16])=[NH:15])[CH2:9][CH3:10].C([O:23][CH:24]=[C:25]([C:31](OCC)=O)[C:26]([O:28][CH2:29][CH3:30])=[O:27])C.O>C(O)C.C(O)(=O)C>[O:23]=[C:24]1[NH:16][C:14]([C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[O:11][CH2:8][CH2:9][CH3:10])=[N:15][CH:31]=[C:25]1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6871Diethyl (ethoxymethylene)malonateHCID 5360545SodiumHCID 86734867n-Propoxybenzamidine methyl sulfate

Produkt 1

HCID 12535801Ethyl 1,6-dihydro-6-oxo-2-(2-propoxyphenyl)pyrimidine-5-carboxylateAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a warm solution of sodium (181.7 g., 7.9 g-atoms) in ethanol (5 l) was added with stirring a slurry of 2-n-propoxybenzamidine methyl sulfate (1146.7 g., 3.95 moles) in ethanol 1.6 l). After 2-3 minutes diethyl ethoxymethylenemalonate 854 g., 3.95 moles) was added and the mixture stirred and heated under reflux for 2.25 hours. The mixture was cooled and then added to cold water (13 l). The mixture was acidified to pH 5-6 with glacial acetic acid. The solid was collected by filtration, washed with water, and dried to give the title compound (937.8 g.), m.p. 102°-104°. An additional crop of product (101.6 g., m.p. 105°-107°, was obtained from the filtrate and washings. Total yield of product, 1039.4 g. (87%).

Aufarbeitung

  1. addition, 3.95 moles) was added
  2. temperatureheated
  3. temperatureunder reflux for 2.25 hours
  4. temperatureThe mixture was cooled
  5. filtrationThe solid was collected by filtration
  6. washwashed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-065927c40061460988df48a29522d551
Quelldatensatz
uspto-grants-1978_04
Patentnummer
US04082751

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