Water → 6-Chloro-2-hydroxy-3-nitrobenzenesulfonamide

HRID 396277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 396277
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[S:12]([NH2:15])(=[O:14])=[O:13].[H-].[Na+].[OH2:18]>C(OCC)(=O)C>[Cl:11][C:4]1[C:3]([S:12]([NH2:15])(=[O:14])=[O:13])=[C:2]([OH:18])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 962Water2×HCID 24758Sodium hydrideHCID 111732852,6-Dichloro-3-nitrobenzene-1-sulfonamide

Produkt 1

HCID 112768176-Chloro-2-hydroxy-3-nitrobenzenesulfonamideAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A mixture of 2,6-dichloro-3-nitrobenzenesulfonamide (2.61 g, 9.64 mmol), 60% sodium hydride (1.15 g, 28.9 mmol) and water (174 μL, 9.64 mmol) was heated to 45° C. while kept at argon atmosphere for 3 days. The reaction was monitored by 1H NMR. 0.1 equivalent water was added to the mixture when the reaction was not completed. The solvent was evaporated when the reaction almost completed indicated by 1H NMR. The residue was diluted with ethyl acetate and washed with 1N aq. HCl. The solvent was concentrated to give the crude material. Column chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (50/48/2, v/v/v), gave the desired product (1.87 g, 77%). EI-MS (m/z)250.84, 252.89 (M−).

Aufarbeitung

  1. additionwas added to the mixture when the reaction
  2. customThe solvent was evaporated when
  3. customthe reaction
  4. washwashed with 1N aq. HCl
  5. concentrationThe solvent was concentrated
  6. customto give the crude material
  7. washColumn chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (50/48/2, v/v/v)

Quellen und Nachweise

ORD-Eintrag
ord-aa8dcc0cb7e14153906f92d8bb186c5d
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608077B2

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