Hydrochloric Acid → 2-Acetyl-6-chloro-3-nitrobenzenesulfonamide

HRID 2301491Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2301491
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].[C:16]([O-])(=[O:18])[CH3:17].[K+].C1OCCOCCOCCOCCOCCOC1.Cl>CS(C)=O>[C:16]([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])(=[O:18])[CH3:17]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 111732852,6-Dichloro-3-nitrobenzene-1-sulfonamide

Produkt 1

HCID 183734452-Acetyl-6-chloro-3-nitrobenzenesulfonamideAusbeute 79,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of 2,6-dichloro-3-nitrobenzenesulfonamide (2.04 g, 7.5 mmol), potassium acetate (2.21 g, 22.5 mmol) and 18-crown-6 (5.95 g, 22.5 mmol) in 50 mL of dimethyl sulfoxide was heated to 45° C., for 7 days. The mixture was acidified with 1N aq. HCl, and extracted with ethyl acetate. The organic layer was concentrated to give the crude material. Column chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (50/49/1, v/v/v) gave the desired product (1.67 g, 76%). EI-MS (m/z) 293.1, 295.1 (M−).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. customto give the crude material
  4. washColumn chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (50/49/1, v/v/v)

Quellen und Nachweise

ORD-Eintrag
ord-fc4e504cf23c4ab899a31e57d7238369
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06500863B1

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