Reacción #595515

Ecuación de reacción

4-ethynylaniline

pyridine

methanesulfonyl chloride

→

title compound

Rendimiento 80.0%

N-(4-ethynylphenyl)methanesulfonamide

Rendimiento 80.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroIn a 2 L, 3-neck round-bottom flask equipped with an overhead stirrer
2. 2
   Otroto give an orange solution
3. 3
   Lavadowashed with 1M aqueous HCl (3×250 mL)
4. 4
   LavadoThe dichloromethane layer was then washed sequentially with saturated aqueous NaHCO3, water, and saturated aqueous NaCl
5. 5
   SecadoThe dichloromethane layer was dried over sodium sulfate
6. 6
   workup.ADDITIONtreated simultaneously with decolorizing charcoal for 30 min
7. 7
   Filtraciónthe solution then filtered through Celite
8. 8
   Concentraciónthe filtrate was concentrated
9. 9
   workup.DISSOLUTIONThe pink/orange solid was dissolved in a minimal amount of hot ethyl acetate (50-75 mL)
10. 10
    workup.ADDITIONslowly diluted with hexanes (500-600 ml)
11. 11
    Otroto give orange crystals that
12. 12
    Filtraciónwere collected by filtration
13. 13
    Otrodried

Procedimiento

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%).

Fuente