Hydrochloric Acid → N-benzyl-5-hydroxynaphthalene-2-sulfonamide

HRID 1818061Notes

Reaction equation

HRID 1818061 reaction equation
[OH-].[Na+].C([O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11]([S:17]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:19])=[O:18])=[CH:12]2)(=O)C.Cl>C(O)C>[CH2:21]([NH:20][S:17]([C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[CH:14][CH:15]=[CH:16][C:7]=2[OH:6])[CH:12]=1)(=[O:19])=[O:18])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 102370445-acetyloxy-N-benzylnaphthalene-2-sulfonamide

Product 1

HCID 10236623N-benzyl-5-hydroxynaphthalene-2-sulfonamideYield 100.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (3 ml) and 2N aqueous sodium hydroxide (0.1 ml) were added to 5-acetyloxy-N-benzylnaphthalene-2-sulfonamide (Compound No. 3-1; 62.0 mg, 0.17 mmol), and the mixture was stirred at room temperature for 5 minutes. 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=1:1) to give the title compound as a yellow white crystal (53.3 mg, 100%).

Workup

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

Sources & evidence

ORD record
ord-1b126448611143859d12c0625e48a36d
Source dataset
uspto-grants-2009_10
Patent number
US07598418B2

Reaction notes

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