Sodium Hydroxide → 2-Amino-5-(1-hydroxyiminoethyl)benzenesulfonamide

HRID 496103Notes

Reaction equation

HRID 496103 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH2:14])=[C:8]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:9]=1)(=O)[CH3:2].[NH2:15][OH:16].Cl.[OH-].[Na+]>CCO>[NH2:14][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[N:15][OH:16])[CH3:2])=[CH:9][C:8]=1[S:10]([NH2:13])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 129523995-Acetyl-2-aminobenzenesulfonamide2×

Product 1

HCID 1301192852-Amino-5-(1-hydroxyiminoethyl)benzenesulfonamideYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-acetyl-2-aminobenzenesulfonamide (see compound 13) (0.45 g, 2.1 mmol) in 96% EtOH (40 ml) was added H2NOH.HCl (0.28 g, 4 mmol) and 2M NaOH (2 ml). The mixture was boiled for 2 h and the solvent was evaporated. The residue was triturated with water (25 ml) and the product was filtered off and dried, yielding 0.39 g (81%) of 2-amino-5-(1-hydroxyiminoethyl)benzenesulfonamide as yellow powder. The product was further transformed by Method G (using cyclohexanecarboxaldehyde). M.p. 230-233° C.

Workup

  1. customthe solvent was evaporated
  2. customThe residue was triturated with water (25 ml)
  3. filtrationthe product was filtered off
  4. customdried

Sources & evidence

ORD record
ord-ad63d2874d654c51b860a80e0dc737e8
Source dataset
uspto-grants-2005_09
Patent number
US06943159B1

Reaction notes

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