Toluene → HCID 44180853, Verbindung

HRID 1042033

Reaktionsgleichung

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[O:8][C:9]3[C:14]([C:15](=O)[CH:16]=2)=[CH:13][CH:12]=[CH:11][C:10]=3[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[O:8][C:9]3[C:14]([C:15](=[S:33])[CH:16]=2)=[CH:13][CH:12]=[CH:11][C:10]=3[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:3][CH2:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

A 2 mL conical microwave vial was charged with a magnetic stirring bar, 2-morpholino-8-phenyl-4H-chromen-4-one (LY294002) (150 mg, 488 μmol), Lawesson's reagent (118 mg, 293 μmol), and toluene (2 mL). The reaction mixture was sealed, and the reaction mixture was magnetically stirred and heated via microwave irradiation to 130° C. for 20 minutes. The final mixture was poured onto water (approximately 30 mL), extracted with dichloromethane (3×5 mL), the combined extracts dried over anhydrous magnesium sulfate, filtered and concentrated to dryness. Purification via column chromatography (silica gel; hexanes/ethyl acetate (1:1), then 100% ethyl acetate) afforded pure 2-morpholino-8-phenyl-4H-chromene-4-thione (68) (128 mg, 81% yield).

Aufarbeitung

additionA 2 mL conical microwave vial was charged with a magnetic stirring bar
customThe reaction mixture was sealed
extractionextracted with dichloromethane (3×5 mL)
dry with materialthe combined extracts dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated to dryness
customPurification via column chromatography (silica gel

Quellen und Nachweise

ORD-Eintrag: ord-ab050b876fc049279c98c58122f878ad
Quelldatensatz: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08557807B2

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