Ethanolamine → 4-Bromo-N-(2-hydroxyethyl)benzene-1-sulfonamide

Temperature

0 °C

To a stirred solution of 4-bromo-benzenesulfonyl chloride (1.00 g, 3.92 mmol) in methylene chloride (25 mL) was added N,N-dimethylaminopyridine (0.608 g, 4.98 mmol). The reaction mixture was cooled to 0° C., and ethanolamine (0.287 g, 4.70 mmol) was added dropwise. After stirring for 30 minutes, the reaction mixture was quenched with water (15 mL). The resulting mixture was extracted with methylene chloride (3×25 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. Purification using silica gel chromatography (100-200 mesh, 10-15% ethyl acetate-hexane) provided 4-bromo-N-(2-hydroxy-ethyl)-benzenesulfonamide. MS calcd. for C8H11BrNO3S [(M+H)+] 281, obsd. 282.2.

1. customthe reaction mixture was quenched with water (15 mL)
2. extractionThe resulting mixture was extracted with methylene chloride (3×25 mL)
3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
4. concentrationconcentrated under reduced pressure
5. customto give the crude product
6. customPurification

ORD record

ord-8e17875e95314460a401b03d2b87e612

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000044B2