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

HRID 6182

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][CH2:17][S:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.[CH2:25]1[CH2:35][CH2:34][N:33]2C(=NC[CH2:31][CH2:32]2)CC1.O>CN(C)C=O>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[S:18][CH2:17][CH2:16][CH2:15][CH2:14][N:12]1[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[C:7](=[O:8])[N:9]([CH2:14][CH2:15][CH2:16][CH2:17][S:18][C:32]2[CH:31]=[CH:25][CH:35]=[CH:34][N:33]=2)[C:10]1=[O:11]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 1.62 g (10 mmol) of benzoylene urea and 2.02 g (10 mmol) of 2-(4-chlorobutylthio)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: hexane/ethyl acetate =2:1 to 1:2). First, 221 mg of the desired product was obtained (4.6% yield, yellow oil), and then, 292 mg of 3-[4-(2-pyridylthio)butyl]quinazoline-2,4(1H,3H)-dione was obtained (8.9% yield, white crystals).

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: hexane/ethyl acetate =2:1 to 1:2)

Quellen und Nachweise

ORD-Eintrag: ord-9bc7f16969ba4b2985a63d53dcd01956
Quelldatensatz: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05246948

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