N,N-Dimethylaniline → 3-(Dimethylamino)benzene-1-sulfonyl chloride

Temperature

0 °C

Sulfurochloridic acid (100 g, 862.07 mmol) was cooled to 0° C. and N,N-dimethylbenzenamine (20 g, 165.29 mmol) was added dropwise with stirring, maintaining a temperature of 0° C. The resulting solution was then heated to 120° C. and stirred for 3 hours. After cooling to room temperature, dichloromethane (40 mL) was added and the resulting mixture was added dropwise to 100 mL of ice/salt water. The resulting solution was extracted with dichloromethane (3×500 mL) and the organic layers combined, dried (Na2SO4) and filtered. The filtrate was concentrated and the residue was purified by column chromatography using a 1:100 ethyl acetate/petroleum ether solvent system. The collected fractions were combined and concentrated to give 4.1 g (11%) of 3-(dimethylamino) benzene-1-sulfonyl chloride as a yellow solid. 1H NMR (CDCl3) δ 7.41 (t, 1H), 7.31 (d, 1H), 7.23 (s, 1H), 6.98 (m, 1H), 3.05 (s, 6H).

1. temperatureThe resulting solution was then heated to 120° C.
2. stirringstirred for 3 hours
3. temperatureAfter cooling to room temperature
4. extractionThe resulting solution was extracted with dichloromethane (3×500 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationThe filtrate was concentrated
8. customthe residue was purified by column chromatography
9. concentrationconcentrated

ORD record

ord-4d938b0c917b4dff89a252b9fe590690

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696229B2