2-Fluoro-5-nitrobenzene-1-sulfonamide → 5-amino-2-fluorobenzenesulfonamide

HRID 2408370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2408370
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][C:10]=1[F:11])(=[O:4])=[O:3]>ClCCl.CO.[Pd]>[NH2:12][C:7]1[CH:8]=[CH:9][C:10]([F:11])=[C:5]([S:2]([NH2:1])(=[O:3])=[O:4])[CH:6]=1

Komponenten

5

Edukt 1

HCID 77303242-Fluoro-5-nitrobenzene-1-sulfonamide

Produkt 1

HCID 432553875-amino-2-fluorobenzenesulfonamideAusbeute 77,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-aminosulfonyl-4-fluoronitrobenzene (360 mg, 1.62 mmol) in dichloromethane (6 mL) and methanol (3 mL) was added 10% Pd/C (36 mg) and shaken under a hydrogen atmosphere at 50 psi for 15 minutes. The mixture was filtered through Celite and the cake was washed with methanol (5 mL). The combined organic solvent was concentrated under reduced pressure to give crude product, which was further purified by flash column chromatography (ethyl acetate:hexanes 1:1) to give 240 mg of 5-amino-2-fluorobenzensulfonamide as a light yellow solid. 1H NMR (DMSO-d6): δ 7.38 (s, 2H), 7.03-6.94 (m, 2H), 6.70-6.66 (m, 1H), 5.33 (s, 1H).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. washthe cake was washed with methanol (5 mL)
  3. concentrationThe combined organic solvent was concentrated under reduced pressure
  4. customto give crude product, which
  5. customwas further purified by flash column chromatography (ethyl acetate:hexanes 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-85d2b673606641e7a337254ed44cd0aa
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815848B2

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