P-Anisidine → 4-Fluoro-1-[(4-methoxyphenyl)aminosulfonyl]-3-nitrobenzene

HRID 1936198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1936198
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]>CO>[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:19])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]

Komponenten

4

Edukt 2

HCID 7732P-AnisidineHCID 27827994-Fluoro-3-nitrobenzene-1-sulfonyl chloride

Produkt 1

HCID 155506334-Fluoro-1-[(4-methoxyphenyl)aminosulfonyl]-3-nitrobenzeneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

p-Anisidine (760 mg, 6.18 mmol) was added to a solution of 4-fluoro-3-nitrophenylsulfonyl chloride (740 mg, 3.09 mmol; Example A) in MeOH (10 ml) at ambient temperature. After stining at room temperature for 15 min, the reaction mixture was concentrated under reduced pressure and the residue was taken up in ethyl acetate and filtered through a pad of silica gel. Concentration of the filtrate, followed by chromatography, provided 603 mg (60% yield) of the title compound. 1H-NMR (CDCl3): δ 8.42 (1H, dd, J=2.3, 6.8 Hz), 7.88 (1H, ddd, J=2.4, 4.0, 8.8 Hz), 7.33 (1H, dd, J=8.8, 9.9 Hz), 6.98 (2H, m), 6.81 (2H, m), 6.45 (1H, s), 3.77 (3H, s). MS (EI): 326 (11, M+), 122 (100). Anal. Calcd. for C13H11FN2O5S: C, 47.85; H, 3.40; N, 8.59; S, 9.83. Found: C, 47.68; H, 3.44; N, 8.54; S, 9.88.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. filtrationfiltered through a pad of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-1a793013bf3144bbb0c0e8a6ff0b4c24
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06388131B2

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