Water → 3-[3-(4-pyridylthio)propyl]quinazoline-2,4(1H,3H)-dione

HRID 864020

Reaktionsgleichung

[CH:1]1[CH:6]=[C:5]2[C:7]([NH:9][C:10]([NH:12][C:4]2=[CH:3][CH:2]=1)=[O:11])=[O:8].Cl[CH2:14][CH2:15][CH2:16][S:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.C1CCN2C(=NCCC2)CC1.O>CN(C)C=O>[N:21]1[CH:22]=[CH:23][C:18]([S:17][CH2:16][CH2:15][CH2:14][N:9]2[C:7](=[O:8])[C:5]3[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=3)[NH:12][C:10]2=[O:11])=[CH:19][CH:20]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 1.62 g (10 mmol) of benzoylene urea and 1.88 g (10 mmol) of 4-(3-chloropropylthio)pyridine in 50 ml of dimethylformamide, 1.65 ml (11 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, and the mixture was stirred at 80° C. for 16 hours. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was distilled off. The residue was purified by column chromatography (eluent:ethyl acetate/ethanol=25:1 to 10:1 to 2:1). First, 0.973 g of 3-[3-(4-pyridylthio)propyl]quinazoline-2,4-(1H,3H)-dione (31.1% yield, pale yellow crystals) was obtained, and then, 0.487 g of the desired product was obtained (10.4% yield, yellow oil).

Aufarbeitung

temperatureAfter cooling
extractionthe mixture was extracted with ethyl acetate
customThe extract was dried
distillationthe solvent was distilled off
customThe residue was purified by column chromatography (eluent:ethyl acetate/ethanol=25:1 to 10:1 to 2:1)

Quellen und Nachweise

ORD-Eintrag: ord-23d280a50411417ca88c8e86ccf73a33
Quelldatensatz: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05561147

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