Sulfuric Acid → 6-Nitrosaccharin

HRID 1038797

Reaktionsgleichung

Reaktionsgleichung von HRID 1038797
S(=O)(=O)(O)[OH:2].[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[S:16]([NH2:19])(=[O:18])=[O:17]>O>[N+:13]([C:10]1[CH:11]=[CH:12][C:7]2[C:6](=[O:2])[NH:19][S:16](=[O:18])(=[O:17])[C:8]=2[CH:9]=1)([O-:15])=[O:14]

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 2342822-Methyl-5-nitrobenzene-1-sulfonamide

Produkt 1

HCID 1001876-NitrosaccharinAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of CrO3 (20.8 g, 208 mmol) in water (150 mL) was slowly added concentrated sulfuric acid (190 mL). To the resulting mixture was added 2-methyl-5-nitrobenzenesulfonamide (10.0 g, 46.3 mmol) and the mixture was stirred at rt for about 42 h. The mixture was filtered and the filter cake was washed with water (100 mL). The solid was dissolved in 10% aqueous NaHCO3, filtered and the filtrate acidified with 2 N HCl (pH=1). The precipitate was collected by filtration and washed with water (2×50 mL) to provide 6-nitro-1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[d]isothiazol-3-one (7.2 g, 68%). 1H NMR (DMSO-d6) δ: 8.42-8.53 (m, 2H), 8.00 (s, 1H), 3.70 (br s, 1H).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with water (100 mL)
  3. dissolutionThe solid was dissolved in 10% aqueous NaHCO3
  4. filtrationfiltered
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water (2×50 mL)

Quellen und Nachweise

ORD-Eintrag
ord-8021f79441024130ba2d13f8e98798c0
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551981B2

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