Benzenesulfonyl chloride → HCID 66906833, Verbindung

HRID 2405868Notizen

Reaktionsgleichung

Cl.[Br:2][C:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[S:5][C:4]=1[NH2:12].[C:13]1([S:19]([Cl:22])(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[ClH:22].[Br:2][C:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[S:5][C:4]=1[NH:12][S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of compound 145-H (0.46 g, 1.52 mmol) in pyridine (4.6 mL), cooled to 0° C., was added benzenesulfonyl chloride (0.206 mL, 1.60 mmol), and the reaction was heated to 50° C. for 72 h. Additional benzenesulfonyl chloride (0.412 mL, 3.20 mmol) was added and the reaction mixture was heated at 50° C. for an additional 16 h. The solvent was evaporated in vacuo, the residue dissolved in dichloromethane and washed with aqueous sodium bicarbonate. The aqueous layer was acidified with 1N HCl, extracted with dichloromethane, and the organic layer was evaporated in vacuo to afford a yellow solid (0.22 g, 36%) as a 1/3.5 mixture of the 3-bromo- and 3-chloro-substituted compounds, 145-Ia and 145-Ib, respectively. 1H-NMR (DMSO-d6): δ 7.1-7.2 (m, 1H), 7.4-7.6 (m, 3H), 7.8 (m, 2H), 8.1-8.2 (m, 1H), 8.25-8.35 (m, 1H); MS: m/z 465 and 509 (MH+).

Aufarbeitung

temperaturethe reaction mixture was heated at 50° C. for an additional 16 h
customThe solvent was evaporated in vacuo
dissolutionthe residue dissolved in dichloromethane
washwashed with aqueous sodium bicarbonate
extractionextracted with dichloromethane
customthe organic layer was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-1758dafa91834e5babffa943f9776eac
Quelldatensatz: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08809327B2

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