Benzenesulfonyl chloride → Benzenesulfonamide

To an ice cold stirred solution of p-toluidine (5.00 g, 47 mmol) and triethylamine (6.5 ml, 51 mmol) in dry THF (100 ml) under argon was slowly added benzenesulphonyl chloride (5.9 ml, 47 mmol). A white precipitate formed. The ice bath was removed and the reaction stirred at ambient temperature for four hours. THF was evaporated under reduced pressure and the resulting oil partitioned between ethyl acetate (100 ml) and 2M hydrochloric acid (100 ml). The organic layer was separated and washed with 2M hydrochloric acid (3×75 ml), water (75 mi), 5% sodium hydrogen carbonate (3×75 ml) and finally water (75 ml). 4-he solution was then dried over MgSO4, filtered and evapourated to give the crude sulphonamide, which was crystallised from ethyl acetate/hexane to give N-4-methylbenzll phenylsulphonamide (9.8 g, 85%) as a white crystalline solid.

1. customA white precipitate formed
2. customThe ice bath was removed
3. customTHF was evaporated under reduced pressure
4. customthe resulting oil partitioned between ethyl acetate (100 ml) and 2M hydrochloric acid (100 ml)
5. customThe organic layer was separated
6. washwashed with 2M hydrochloric acid (3×75 ml), water (75 mi), 5% sodium hydrogen carbonate (3×75 ml) and finally water (75 ml)
7. dry with material4-he solution was then dried over MgSO4
8. filtrationfiltered
9. customto give the crude sulphonamide, which
10. customwas crystallised from ethyl acetate/hexane

ORD record

ord-755f172721fa49c68dd3c18f94b7c728

Source dataset

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05314880