Hydrochloric Acid → HCID 10171893, compound

HRID 1818059Notes

Reaction equation

HRID 1818059 reaction equation
[OH-].[Na+].CC1C=CC(S([O:13][C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH:16]=[CH:17][CH:18]=[C:19]3[S:24]([NH2:27])(=[O:26])=[O:25])(=O)=O)=CC=1.Cl>CO>[CH2:16]([NH:27][S:24]([C:19]1[C:20]2[C:15](=[C:14]([OH:13])[CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:17][CH:18]=1)(=[O:25])=[O:26])[C:15]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86600815HCID 86600815, compound

Product 1

HCID 10171893HCID 10171893, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Methanol (5 ml) and 5N aqueous sodium hydroxide (0.65 ml) were added to 5-{[(4-methylphenyl)sulfonyl]oxy}naphthalene-1-sulfonamide (Compound No. 1-1; 298.8 mg, 0.64 mmol), and the mixture was stirred at 65° C. for 1 hour. After cooling to room temperature, the reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (eluent; n-hexane : ethyl acetate=3:2→1:1) to give the title compound as a light brown white crystal (152.8 mg, 76.2%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washAfter the organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe residue obtained by evaporation of the solvent under reduced pressure
  6. customwas purified by column chromatography on silica gel (eluent; n-hexane : ethyl acetate=3:2→1:1)

Sources & evidence

ORD record
ord-e0539c60838c4f23a1fd9b5a8f26806e
Source dataset
uspto-grants-2009_10
Patent number
US07598418B2

Reaction notes

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