Pyridine → N-(4-ethynylphenyl)methanesulfonamide

In a 2 L, 3-neck round-bottom flask equipped with an overhead stirrer was added 4-ethynylaniline (30 g, 256 mmol) and pyridine (42.5 ml, 525 mmol) in dichloromethane (512 ml) to give an orange solution. The mixture was cooled to 5° C. and methanesulfonyl chloride (19.96 ml, 256 mmol) was added drop wise over 15 min. The reaction solution was stirred at 5° C. for 2 h and washed with 1M aqueous HCl (3×250 mL). The dichloromethane layer was then washed sequentially with saturated aqueous NaHCO3, water, and saturated aqueous NaCl. The dichloromethane layer was dried over sodium sulfate and treated simultaneously with decolorizing charcoal for 30 min, the solution then filtered through Celite and the filtrate was concentrated. The pink/orange solid was dissolved in a minimal amount of hot ethyl acetate (50-75 mL) and slowly diluted with hexanes (500-600 ml) to give orange crystals that were collected by filtration and dried to provide the title compound (40.0 g, 80%).

1. customIn a 2 L, 3-neck round-bottom flask equipped with an overhead stirrer
2. customto give an orange solution
3. washwashed with 1M aqueous HCl (3×250 mL)
4. washThe dichloromethane layer was then washed sequentially with saturated aqueous NaHCO3, water, and saturated aqueous NaCl
5. dry with materialThe dichloromethane layer was dried over sodium sulfate
6. additiontreated simultaneously with decolorizing charcoal for 30 min
7. filtrationthe solution then filtered through Celite
8. concentrationthe filtrate was concentrated
9. dissolutionThe pink/orange solid was dissolved in a minimal amount of hot ethyl acetate (50-75 mL)
10. additionslowly diluted with hexanes (500-600 ml)
11. customto give orange crystals that
12. filtrationwere collected by filtration
13. customdried

ORD record

ord-6e934627009e400993a87ae77b3367df

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685991B2