Hydrochloric Acid → 2-(Phenylsulfonyl)benzenesulfonyl chloride

HRID 1977959Notes

Reaction equation

HRID 1977959 reaction equation
[C:1]1([S:7]([C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2N)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N([O-])=O.[Na+].[S:21]([O-:25])([O-])(=O)=[O:22].S(=O)(O)[O-].[Na+].[ClH:31]>O>[C:1]1([S:7]([C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[S:21]([Cl:31])(=[O:25])=[O:22])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 1117Sulfate IonHCID 77956Benzenamine, 2-(phenylsulfonyl)-HCID 23665763Sodium BisulfiteHCID 23668193Sodium Nitrite

Product 1

HCID 155615862-(Phenylsulfonyl)benzenesulfonyl chlorideYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-(phenylsulfonyl)aniline (2.33 g, (10 mmol) in 30% aqueous hydrochloric acid (4 mL) was added 40% aqueous sodium nitrite (4 mL) at 0-5° C. After 15 minute, to the diazo solution were added 30% aqueous hydrochloric acid (10 mL), cooper sulfate (50 mg) and 40% aqueous sodium bisulfite (10 mL) at 5-10° C. The mixture was stirred for 30 minutes and additional water (30 mL) was added. The mixture was extracted into dichloromethane (3×40 mL) and the dichloromethane solution was washed with brine (40 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane) to give the title compound as a white solid (2.1 g, 66%). 1H-NMR (300 MHz, CDCl3) δ8.62 (d, J=7.8 Hz, 1H), 8.34 (d, J=7.9 Hz, 1H), 7.85-7.98 (m, 4H), 7.48-7.63 (m, 3H).

Workup

  1. extractionThe mixture was extracted into dichloromethane (3×40 mL)
  2. washthe dichloromethane solution was washed with brine (40 mL)
  3. dry with materialdried over Na2SO4
  4. customAfter removing the solvent in vacuo
  5. customthe residue was purified by flash column chromatography (dichloromethane)

Sources & evidence

ORD record
ord-0c661e5d1f924ee4a2dbb397d78ce676
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

Loading…