2-Chloro-1,4-naphthoquinone → N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide

HRID 1258379

Reaktionsgleichung

[Cl:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=O)[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[S:19]([NH2:22])(=[O:21])=[O:20]>C(OCC)(=O)C>[Cl:1][C:2]1[C:3](=[O:13])[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10](=[N:22][S:19]([C:15]2[S:14][CH:18]=[CH:17][CH:16]=2)(=[O:21])=[O:20])[CH:11]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

385.2 mg 2-chloro-1,4-naphthoquinone (11) was mixed with 326.4 mg thiophene-2-sulfonamide in 15 ml dichloromethylene, to which at 0° C. was added 2 ml TiCl4 dichloromethylene solution followed by 613.3 μl. The mixture was heated at 60° C. with M.W. for 15 min and the black mixture was poured into 100 ml ethyl acetate. The insoluble was removed by filtrate through a pad of celite. The filtrate was concentrated and the residue was suspended in dichloromethylene. The brown insoluble stuff was removed by filtration and the filtrate was again concentrated to dryness. The residue was suspended in ethyl acteate/hexane (1:1) and the yellow solid was filtered. The solid was washed with ethyl acteate/hexane (1:1) and dried over vacuum affording title compound 377.7 mg (55.9%) as a yellow solid. When TiCl4.2THF and THF were used instead, the reaction afforded the title compound 522 mg (77.3%) as a yellow solid, m.p.: 167-169° C.

Aufarbeitung

customThe insoluble was removed by filtrate through a pad of celite
concentrationThe filtrate was concentrated
customThe brown insoluble stuff was removed by filtration
concentrationthe filtrate was again concentrated to dryness
filtrationthe yellow solid was filtered
washThe solid was washed with ethyl acteate/hexane (1:1)
customdried over vacuum

Quellen und Nachweise

ORD-Eintrag: ord-2bcc240fbb1f45b79d13853668afa919
Quelldatensatz: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08466157B2

Verknüpfte Notizen

Wird geladen…