Reaction #57444

Reaction equation

sulfonyl chloride

O-Benzylhydroxylamine hydrochloride

4-methoxybenzenesulfonyl chloride

O-Benzylhydroxylamine hydrogen chloride

diisopropylethylamine

diisopropylethylamine

→

off-white colored solid

Yield 107.1%

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

Yield 107.1%

Solvents

THF

Conditions

Workup

1. 1
   Temperatureto warm to room temperature
2. 2
   workup.STIRRINGThe reaction stirred for 4 additional hours at room temperature
3. 3
   ConcentrationThe reaction solution was concentrated to a solid
4. 4
   Otherpartitioned between ethyl acetate and 1N HCl
5. 5
   DryingThe organic layer was dried over magnesium sulfate
6. 6
   Concentrationconcentrated under vacuum

Procedure

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).

Source