Sulfuric Acid → HCID 11150443, compound

HRID 532475Notes

Reaction equation

HRID 532475 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[I:7][C:8]1[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.[OH-].[Na+].OS(O)(=O)=O>O.O1CCOCC1>[I:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([OH:16])=[O:15])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 73994-Iodobenzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 11150443HCID 11150443, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of sodium carbonate (9.4 g, 74.375 mmol) in water (30 mL, 10 v/w) was dropwise added to a solution of 4-iodo-benzenesulfonyl chloride (3 g, 9.917 mmol) in 1,4-dioxane (15 mL, 5 v/w) at room temperature, followed by stirring at room temperature for 30 min. Then, 1N aqueous sodium hydroxide was dropwise added thereto so as to adjust the pH of the reaction mixture to 14, followed by stirring at room temperature for 12 hours. The reaction mixture was cooled to 0° C., and conc. H2SO4 solution was dropwise to adjust the pH of the reaction mixture to 1. The reaction mixture was extracted three times with ethyl acetate, and the organic layer thus obtained was washed with water. The washed layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (2.5 g).

Workup

  1. stirringby stirring at room temperature for 12 hours
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. extractionThe reaction mixture was extracted three times with ethyl acetate
  4. customthe organic layer thus obtained
  5. washwas washed with water
  6. dry with materialThe washed layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-727395fbf8e046f1987a453c0a80888b
Source dataset
uspto-grants-2014_10
Patent number
US08853213B2

Reaction notes

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