Water → 6-Chloro-2-hydroxy-3-nitrobenzenesulfonamide

HRID 396277Notes

Reaction equation

HRID 396277 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[S:12]([NH2:15])(=[O:14])=[O:13].[H-].[Na+].[OH2:18]>C(OCC)(=O)C>[Cl:11][C:4]1[C:3]([S:12]([NH2:15])(=[O:14])=[O:13])=[C:2]([OH:18])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 24758Sodium hydrideHCID 111732852,6-Dichloro-3-nitrobenzene-1-sulfonamide

Product 1

HCID 112768176-Chloro-2-hydroxy-3-nitrobenzenesulfonamideYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 2,6-dichloro-3-nitrobenzenesulfonamide (2.61 g, 9.64 mmol), 60% sodium hydride (1.15 g, 28.9 mmol) and water (174 μL, 9.64 mmol) was heated to 45° C. while kept at argon atmosphere for 3 days. The reaction was monitored by 1H NMR. 0.1 equivalent water was added to the mixture when the reaction was not completed. The solvent was evaporated when the reaction almost completed indicated by 1H NMR. The residue was diluted with ethyl acetate and washed with 1N aq. HCl. The solvent was concentrated to give the crude material. Column chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (50/48/2, v/v/v), gave the desired product (1.87 g, 77%). EI-MS (m/z)250.84, 252.89 (M−).

Workup

  1. additionwas added to the mixture when the reaction
  2. customThe solvent was evaporated when
  3. customthe reaction
  4. washwashed with 1N aq. HCl
  5. concentrationThe solvent was concentrated
  6. customto give the crude material
  7. washColumn chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (50/48/2, v/v/v)

Sources & evidence

ORD record
ord-aa8dcc0cb7e14153906f92d8bb186c5d
Source dataset
uspto-grants-2003_08
Patent number
US06608077B2

Reaction notes

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