反応 #57444

反応方程式

sulfonyl chloride

O-Benzylhydroxylamine hydrochloride

4-methoxybenzenesulfonyl chloride

O-Benzylhydroxylamine hydrogen chloride

diisopropylethylamine

diisopropylethylamine

→

off-white colored solid

収率 107.1%

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

収率 107.1%

溶媒

THF

反応条件

後処理

1. 1
   温度to warm to room temperature
2. 2
   workup.STIRRINGThe reaction stirred for 4 additional hours at room temperature
3. 3
   濃縮The reaction solution was concentrated to a solid
4. 4
   その他partitioned between ethyl acetate and 1N HCl
5. 5
   乾燥The organic layer was dried over magnesium sulfate
6. 6
   濃縮concentrated under vacuum

実験手順

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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