1,1'-Thiocarbonyldi-2(1H)-pyridone → 6,8-Dichloro-3-isothiocyanatoisoquinoline

HRID 1875981

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH:8]=[N:7][C:6]([NH2:13])=[CH:5]2.[C:14](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:15]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH:8]=[N:7][C:6]([N:13]=[C:14]=[S:15])=[CH:5]2

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

To 6,8-dichloroisoquinolin-3-amine (0.27 g, 1.28 mmol) in dichloromethane (20 mL) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (0.30 g, 1.29 mmol) and the reaction mixture was stirred at 40° C. for 4 hours. The reaction was cooled to room temperature and chromatographed (Biotage: 10-100% ethyl acetate/hexanes) to yield 6,8-dichloro-3-isothiocyanatoisoquinoline (0.2 g, 0.78 mmol, 61.9% yield) as a powder. 1H NMR (500 MHz, DMSO-D6) δ ppm 9.42 (s, 1H), 8.16 (d, J=1.83 Hz, 1H), 8.02 (d, J=2.14 Hz, 1H), 7.92 (s, 1H). MS (LC/MS) R.T.=3.63; [M+H]+=255.0.

Aufarbeitung

temperatureThe reaction was cooled to room temperature
customchromatographed (Biotage: 10-100% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-3e33465b086b446bb298b9f72faef9d5
Quelldatensatz: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08309577B2

Verknüpfte Notizen

Wird geladen…