반응 #57439

반응 방정식

THF

O-phenylhydroxylamine hydrochloride

4-methoxybenzenesulfonyl chloride

diisopropylethylamine

→

4-methoxy-N1-phenoxy-1-benzenesulfonamide

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   기타the flask was re-sealed
2. 2
   workup.WAITAfter another 2 hours
3. 3
   workup.STIRRINGthe reaction stirred for an additional 15 hours
4. 4
   농축The resulting red solution was concentrated to an oil
5. 5
   기타partitioned between ethyl acetate and 1N HCl
6. 6
   기타The organic layer was separated
7. 7
   세척washed with saturated aqueous sodium bicarbonate and brine
8. 8
   건조dried over magnesium sulfate
9. 9
   농축concentrated under vacuum
10. 10
    기타The resulting dark brown residue was purified by silica gel chromatography (3:1 hexanes/ethyl acetate)
11. 11
    기타providing 360 mg (21%) of a redish solid

실험 절차

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): δ 7.89 (2H,d), 7.30-7.20 (3H,m), 7.11 (2H,d), 7.02 (1H,s), 7.00 (2H,d), 3.88 (3H,s).

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