Acetone → HCID 23697072, compound

HRID 2068002Notes

Reaction equation

HRID 2068002 reaction equation
S([O-])([O-])=O.[Na+:5].[Na+].CC(C)=O.[CH3:11][C:12]1[C:16]([S:17](Cl)(=[O:19])=[O:18])=[C:15]([CH3:21])[O:14][N:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:11][C:12]1[C:16]([S:17]([O-:19])=[O:18])=[C:15]([CH3:21])[O:14][N:13]=1.[Na+:5]

Participants

6

Reactant 4

HCID 180AcetoneHCID 10340Sodium CarbonateHCID 24437Sodium SulfiteHCID 27363193,5-Dimethylisoxazole-4-sulfonyl chloride

Product 1

HCID 23697072HCID 23697072, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of sodium sulfite (680 mg, 5.40 mmol) in water (5 mL) was added to an acetone (5 mL) solution of 3,5-dimethylisoxazole-4-sulfonyl chloride (530 mg, 2.70 mmol). The mixture was heated to 80° C., then a solution of sodium carbonate (430 mg, 4.05 mmol) in water (5 ml) was added dropwise. The mixture was refluxed for 16 hours then evaporated to dryness. The residue was refluxed with ethanol (20 mL), the inorganics were removed by filtration. Evaporation of the filtrate afforded 500 mg of crude sodium 3,5-dimethylisoxazole-4-sulfinate. It was used in the next steps without further purification. 1H NMR (400 MHz, DMSO-d6): δ 2.37 (s, 3H) and 2.22 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. customthen evaporated to dryness
  3. temperatureThe residue was refluxed with ethanol (20 mL)
  4. customthe inorganics were removed by filtration
  5. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-16cc4349b324424487aa1cf4f126e3ad
Source dataset
uspto-grants-2012_10
Patent number
US08293919B2

Reaction notes

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