4-Thioureidoanisole → 2,3-dihydro-1-(4-methoxyphenyl)-6-methyl-2-thioxo-4(1H)pyrimidinone

HRID 1588480

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH2:12])=[S:11])=[CH:5][CH:4]=1.CC1[O:19][C:18](=O)[CH2:17][C:16](C)([CH3:21])O1.O1C=COCC1=O>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:16]([CH3:21])=[CH:17][C:18](=[O:19])[NH:12][C:10]2=[S:11])=[CH:7][CH:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

N-(4-Methoxyphenyl)thiourea (18.2 g, 100 mM) and 2,6,6-trimethyl-1,3-dioxin-4-one (21.3 g, 150 mM) were heated together at 140° C. (bath temperature) for 30 minutes. The solid product was cooled, treated with ethanol (100 ml), boiled for 10 minutes, cooled and the solid product was isolated by filtration. More dioxinone (21.3 g) was added to the above material and the mixture was heated at 140° C. for a further 20 minutes. Ethanol (50 ml) was then added to the cooled mixture, which was then heated under reflux for 5 minutes. The mixture was cooled and the solid product isolated by filtration to give 2,3-dihydro-1-(4-methoxyphenyl)-6-methyl-2-thioxo-4(1H)pyrimidinone (17.9 g, 72% yield) m.p. 248°-249° C.; microanalysis, found: C,58.2; H,4.9; N,11.0%; C12H12N2OS requires: C,58.1; H,4.8; N,11.3%.

Aufarbeitung

temperatureThe solid product was cooled
temperaturecooled
customthe solid product was isolated by filtration
temperaturewas then heated
temperatureunder reflux for 5 minutes
temperatureThe mixture was cooled
customthe solid product isolated by filtration

Quellen und Nachweise

ORD-Eintrag: ord-45c7ca5e7ed24446a4304ccee2310eb7
Quelldatensatz: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05223505

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