4-Methoxybenzenesulfonyl chloride → 4-methoxy-N1-phenoxy-1-benzenesulfonamide

HRID 1166474Notes

Reaction equation

HRID 1166474 reaction equation
Cl.[C:2]1([O:8][NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C.C1COCC1>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH3:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([S:18]([NH:9][O:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)(=[O:20])=[O:19])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 6365179O-Phenylhydroxylamine hydrochloride

Product 1

HCID 590906714-methoxy-N1-phenoxy-1-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

O-phenylhydroxylamine hydrochloride (6.9 mmol, 1.0 g), 4-methoxybenzenesulfonyl chloride (6.2 mmol, 1.29 g), diisopropylethylamine (13.1 mmol, 2.28 mL) and andhydrous THF (15 mL) were combined under nitrogen. After stirring for 2 hours at room temperature, a few crystals of 4-dimethylaminopyridine were added and the flask was re-sealed. After another 2 hours, 4 mL of N,N-dimethylformamide was injected and the reaction stirred for an additional 15 hours. The resulting red solution was concentrated to an oil and partitioned between ethyl acetate and 1N HCl. The organic layer was separated and washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated under vacuum. The resulting dark brown residue was purified by silica gel chromatography (3:1 hexanes/ethyl acetate) providing 360 mg (21%) of a redish solid. H1-NMR (CDCl3): δ7.89 (2H,d), 7.30-7.20 (3H,m), 7.11 (2H,d), 7.02 (1H,s), 7.00 (2H,d), 3.88 (3H,s).

Workup

  1. customthe flask was re-sealed
  2. waitAfter another 2 hours
  3. stirringthe reaction stirred for an additional 15 hours
  4. concentrationThe resulting red solution was concentrated to an oil
  5. custompartitioned between ethyl acetate and 1N HCl
  6. customThe organic layer was separated
  7. washwashed with saturated aqueous sodium bicarbonate and brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe resulting dark brown residue was purified by silica gel chromatography (3:1 hexanes/ethyl acetate)
  11. customproviding 360 mg (21%) of a redish solid

Sources & evidence

ORD record
ord-9b0421d2ac6e49b08f3427d8083bec51
Source dataset
uspto-grants-2003_09
Patent number
US06613743B2

Reaction notes

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