Water → N,N-Dimethyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide

HRID 1840330Notes

Reaction equation

HRID 1840330 reaction equation
[CH3:1][N:2]([CH3:17])[S:3]([C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]([N+:13]([O-:15])=[O:14])[C:7]=1Cl)(=[O:5])=[O:4].[H-].[Na+].[OH2:20]>>[CH3:1][N:2]([CH3:17])[S:3]([C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]([N+:13]([O-:15])=[O:14])[C:7]=1[OH:20])(=[O:5])=[O:4]

Participants

4

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 23447825N,N-Dimethyl-2,6-dichloro-3-nitrobenzenesulfonamide

Product 1

HCID 23447760N,N-Dimethyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamideYield 93%

Conditions

Temperature
35 °C

Procedure

A mixture of N,N-dimethyl-2,6-dichloro-3-nitrobenzenesulfonamide (2.64 g, 8.83 mmol), 60% sodium hydride (1.06 g, 26.5 mmol) and water (191 mg, 10.6 mmol) was heated to 35° C. while kept under argon atmosphere for 16 hours. The solvent was evaporated. when The reaction was almost complete as 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 (40/58/2, v/v/v), gave the desired product (2.3 g, 93%). EI-MS (m/z)279.5 (M−).

Workup

  1. customThe solvent was evaporated
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with 1N aq. HCl
  4. concentrationThe solvent was concentrated
  5. customto give the crude material
  6. washColumn chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (40/58/2, v/v/v)

Sources & evidence

ORD record
ord-685d8de857934db0b0911c0c18b601ee
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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