1-(2-Methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-ethanone → 1-(2-Methyl-4-phenyl-9-thia-1,7-diaza-fluoren-3-yl)-ethanone

HRID 133524

Reaktionsgleichung

[CH3:1][C:2]1[C:14]([C:15](=[O:17])[CH3:16])=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[C:11]3[CH2:10][CH2:9][NH:8][CH2:7][C:6]=3[S:5][C:4]=2[N:3]=1>C1(C=CC2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:1][C:2]1[C:14]([C:15](=[O:17])[CH3:16])=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[C:11]3[C:6](=[CH:7][N:8]=[CH:9][CH:10]=3)[S:5][C:4]=2[N:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

To a stirred solution of 0.70 g (2.17 mmol) 1-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-ethanone in 10 ml diphenylethylene was added 325 mg palladium on charcoal 10%. The mixture was stirred over night at 150° C., and then poured onto ethyl acetate (about 150 ml), and extracted three times aqueous HCl (1M). The combined aqueous phases were basified with K2CO3 until ph=8, and then the product was extracted with ethyl acetate. The combined organic phase were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 1:1) afforded 75 mg (11%) 1-(2-methyl-4-phenyl-9-thia-1,7-diaza-fluoren-3-yl)-ethanone as a light yellow solid. ES-MS m/e (%): 319 (M+H+, 100).

Aufarbeitung

additionpoured onto ethyl acetate (about 150 ml)
extractionextracted three times aqueous HCl (1M)
extractionthe product was extracted with ethyl acetate
dry with materialThe combined organic phase were dried over sodium sulfate
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-14452336198b4e7584a35ac75d147b6a
Quelldatensatz: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07390903B2

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