Pyridine → N-(5-bromo-2-fluoro-4-methoxyphenyl)ethanesulfonamide

HRID 575576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 575576
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[Br:7][C:8]1[C:9]([O:16][CH3:17])=[CH:10][C:11]([F:15])=[C:12]([CH:14]=1)[NH2:13].N1C=CC=CC=1>C(Cl)Cl>[Br:7][C:8]1[C:9]([O:16][CH3:17])=[CH:10][C:11]([F:15])=[C:12]([NH:13][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH:14]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 838222835-Bromo-2-fluoro-4-methoxyaniline

Produkt 1

HCID 118021927N-(5-bromo-2-fluoro-4-methoxyphenyl)ethanesulfonamideAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

At 0° C., ethansulfonylchloride (1.4 g, 10.9 mmol) was added dropwise to a solution of 5-bromo-2-fluoro-4-methoxyaniline (3.5 g, 24.0 mmol) in pyridine (1.3 g, 16.4 mmol) and dry CH2Cl2 (20 mL). After stirring at room temperature for 10 h, CH2Cl2 extractive work up and purification by silica gel chromatography (PE:EA=10:0 to 3:1) gave the title compound (2.5 g, 73.5%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.77 (d, J=8.4 Hz, 1H), 6.73 (d, J=11.6 Hz, 1H), 6.27 (s, 1H), 3.89 (s, 3H), 3.10 (q, J=7.6 Hz, 2H), 1.40 (t, J=7.6 Hz, 3H). LCMS: 334.0 (M+Na)+

Aufarbeitung

  1. customCH2Cl2 extractive work up and purification by silica gel chromatography (PE:EA=10:0 to 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-420c5d89a7444dcba0923988fd21b7a0
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034900B2

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