Sodium Hydroxide → HCID 14476495, compound

HRID 1904954Notes

Reaction equation

HRID 1904954 reaction equation
[CH2:1]1[O:12][C:11]2[CH:10]=[C:9]3[C:5]([CH:6]=[C:7]([S:22](=[O:25])(=[O:24])[NH2:23])[N:8]3S(C3C=CC=CC=3)(=O)=O)=[CH:4][C:3]=2[O:2]1.[OH-].[Na+]>O>[CH2:1]1[O:12][C:11]2[CH:10]=[C:9]3[C:5]([CH:6]=[C:7]([S:22](=[O:24])(=[O:25])[NH2:23])[NH:8]3)=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14476494HCID 14476494, compound

Product 1

HCID 14476495HCID 14476495, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

An initial suspension of 5,6-methylenedioxy-1-benzenesulfonyl-2-sulfamoylindole (2.21 gm, 5.8 mmol) in 40% sodium hydroxide (4 ml, 40 mmol) and water (11 ml) was warmed at 90° C. for 1 hour to give a homogeneous solution. The reaction was cooled to room temperature and the product salt precipitated. This mixture was acidified with conc. HCl and the precipitated producted collected by filtration. This solid was dissolved in ethyl acetate/acetonitrile, and dried (anhydrous Na2SO4). This solution was filtered through a charcoal pad and the solvents evaporated. The residue was triturated with diethyl ether to give the crystalline product (1.1 gm), mp 234°-237° C.

Workup

  1. customto give a homogeneous solution
  2. temperatureThe reaction was cooled to room temperature
  3. customthe product salt precipitated
  4. filtrationthe precipitated producted collected by filtration
  5. dissolutionThis solid was dissolved in ethyl acetate/acetonitrile
  6. dry with materialdried (anhydrous Na2SO4)
  7. filtrationThis solution was filtered through a charcoal pad
  8. customthe solvents evaporated
  9. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-e308b30afcf34f178623c2f7ba78d3c6
Source dataset
uspto-grants-1989_06
Patent number
US04840963

Reaction notes

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