Ethanol → 1,4,5,6-Tetrahydro-5-ethoxycarbonylpyrimidine Hydrochloride

HRID 1653703

Reaktionsgleichung

Reaktionsgleichung von HRID 1653703
Cl.[NH:2]1[CH2:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5][N:4]=[CH:3]1.S(Cl)([Cl:13])=O.[CH2:15](O)[CH3:16]>>[ClH:13].[CH2:15]([O:9][C:8]([CH:6]1[CH2:7][NH:2][CH:3]=[N:4][CH2:5]1)=[O:10])[CH3:16]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 703421841,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochloride

Produkt 1

HCID 200804501,4,5,6-Tetrahydro-5-ethoxycarbonylpyrimidine HydrochlorideAusbeute 63 %

Versuchsvorschrift

1,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochloride (1.5 g, 9.12 mmol) was dissolved in absolute ethanol (40 ml) by heating. The thionyl chloride (1.1 g, 9.16 mmol) was added dropwise with stirring. The resulting solution was refluxed 20h and then evaporated to dryness in vacuo. The residue was taken up in absolute methanol (5 ml) and dry THF (10 ml) was added to induce crystallization, giving 1.1 g (63%) product as white crystals, mp 125°-127° C. 300 MHz nmr confirmed the product. Microanalysis calc.: C 43.64, H 6.75, N 14.55; found: C, 43.43, H 6.58, N 14.40.

Aufarbeitung

  1. temperatureby heating
  2. customevaporated to dryness in vacuo
  3. additiondry THF (10 ml) was added
  4. customcrystallization

Quellen und Nachweise

ORD-Eintrag
ord-0a47118198fe430299b368f7293bee1b
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05403845

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