반응 #57444

반응 방정식

sulfonyl chloride

O-Benzylhydroxylamine hydrochloride

4-methoxybenzenesulfonyl chloride

O-Benzylhydroxylamine hydrogen chloride

diisopropylethylamine

diisopropylethylamine

→

off-white colored solid

수율 107.1%

N1-(benzyloxy)-4-methoxy-1-benzenesulfonamide

수율 107.1%

용매

THF

반응 조건

후처리

1. 1
   온도to warm to room temperature
2. 2
   workup.STIRRINGThe reaction stirred for 4 additional hours at room temperature
3. 3
   농축The reaction solution was concentrated to a solid
4. 4
   기타partitioned between ethyl acetate and 1N HCl
5. 5
   건조The organic layer was dried over magnesium sulfate
6. 6
   농축concentrated under vacuum

실험 절차

O-Benzylhydroxylamine hydrochloride (31.3 mmol, 5.0 g), 4-methoxybenzenesulfonyl chloride (34.5 mmol, 7.12 g) and anhydrous THF (50 mL) were combined under nitrogen. The reaction was cooled to 0° C. and diisopropylethylamine (69.0 mmol, 12.0 mL) was injected. The reaction was allowed to warm to room temperature and continued to stir for 18 hours. An additional 0.25 equivalents of O-Benzylhydroxylamine hydrogen chloride (7.8 mmol, 1.25 g) and 0.75 equivalents of diisopropylethylamine (23.5 mmol, 4.1 mL) were added to encourage complete conversion of the remaining sulfonyl chloride. The reaction stirred for 4 additional hours at room temperature. The reaction solution was concentrated to a solid and partitioned between ethyl acetate and 1N HCl. The organic layer was dried over magnesium sulfate and concentrated under vacuum to yield 9.83 g (76%) of an off-white colored solid. Rf: 0.2 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.84 (2H,d), 7.34 (5H,s) 7.08 (2H,d), 4.92 (2H,s), 3.88 (3H,s).

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