Diethyl Ether → HCID 19978122, Verbindung

HRID 1449511Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1449511
[ClH:1].[CH2:2]([C:5]1[N:9]2[CH2:10][CH2:11][CH2:12][N:13]=[C:8]2[S:7][C:6]=1[C:14]([OH:16])=O)[CH2:3][CH3:4].C(OCC)C>S(Cl)(Cl)=O>[ClH:1].[CH2:2]([C:5]1[N:9]2[CH2:10][CH2:11][CH2:12][N:13]=[C:8]2[S:7][C:6]=1[C:14]([Cl:1])=[O:16])[CH2:3][CH3:4]

Komponenten

4

Edukt 2

HCID 3283Diethyl EtherHCID 67715287HCID 67715287, Verbindung

Produkt 1

HCID 19978122HCID 19978122, VerbindungAusbeute 203,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

In 35 ml of thionyl chloride was suspended 5.3 g of 3-propyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-2-carboxylic acid hydrochloride obtained Example 12, followed by reflux under heating for 40 minutes. The reaction mixture was cooled with ice, and poured into dry diethyl ether. The precipitated crystals were collected by filtration to yield 5.78 g of 3-propyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-2-carbonyl chloride hydrochloride as colorless powder. This powder was suspended in the mixture of 200 ml of pyridine and 20 ml of dimethylformamide. To the mixture were added 3.38 g of 3.5-dichloroaniline and 250 mg of 3,5-dimethyl-aminopyridine, followed by stirring at 60° C. for 18 hours. The reaction mixture was concentrated and to the mixture was added water. The precipitated crystals were collected by filtration, washed successively with water and cold methanol and suspended in ethanol. To the mixture was added saturated hydrogenchloride diethylether. The formed crystals were collected by filtration and recrystallized from ethanol to obtain 3.65 g of the titled compound.

Aufarbeitung

  1. customobtained Example 12
  2. temperatureby reflux
  3. temperatureunder heating for 40 minutes
  4. temperatureThe reaction mixture was cooled with ice
  5. filtrationThe precipitated crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-f98efdc28ef64b518f99773444238554
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05599813

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