Sulfuric Acid → 6-Nitrosaccharin

HRID 1038797

Reaction equation

HRID 1038797 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

HCID 1001876-NitrosaccharinYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-8021f79441024130ba2d13f8e98798c0
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Linked notes

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