Reaction #806273

Reaction equation

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

Yield 68.5%

Solvents

dichloromethane

dichloromethane

dichloromethane

Conditions

Workup

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

Procedure

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.

Source