Reacción #806273

Ecuación de reacción

pyrid-3-ylsulfonyl chloride

triethylamine

1-[bis(4-chlorophenyl)methyl]azetidin-3-ylamine

→

N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}pyrid-3-ylsulfonamide

Rendimiento 68.5%

Disolventes

dichloromethane

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONbefore adding
2. 2
   Lavadois then washed with twice 25 cm3 of distilled water
3. 3
   SecadoThe organic phase is dried over magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated to dryness under reduced pressure (2.7 kPa)
6. 6
   OtroThe residue obtained
7. 7
   Otrois purified by flash chromatography on silica gel [eluant: dichloromethane/methanol (97.5/2.5 by volume)]

Procedimiento

0.79 cm3 of triethylamine is added, at room temperature under an argon atmosphere, to a solution of 0.7 g of 1-[bis(4-chlorophenyl)methyl]azetidin-3-ylamine in 25 cm3 of dichloromethane. The mixture is cooled to around 0° C. before adding thereto a solution of 1.2 g of pyrid-3-ylsulfonyl chloride in 25 cm3 of dichloromethane, and then it is stirred at room temperature for 16 hours. The reaction mixture is diluted with 50 cm3 of dichloromethane and is then washed with twice 25 cm3 of distilled water. The organic phase is dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is purified by flash chromatography on silica gel [eluant: dichloromethane/methanol (97.5/2.5 by volume)]. 0.7 g of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}pyrid-3-ylsulfonamide is obtained in the form of a cream-colored foam which solidifies in the presence of isopropanol into a cream-colored powder melting at 164° C.

Fuente