反応 #806274

反応方程式

4-fluorophenylsulfonyl chloride

triethylamine

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

→

N-{1-[bis(4-chloro-phenyl)methyl]azetidin-3-yl}-4-fluorophenylsulfonamide

収率 38.7%

溶媒

dichloromethane

反応条件

後処理

1. 1
   洗浄the reaction mixture is washed with 10 cm3 of distilled water
2. 2
   乾燥dried over magnesium sulfate
3. 3
   ろ過filtered
4. 4
   濃縮concentrated to dryness under reduced pressure (2.7 kPa)
5. 5
   その他The residue obtained
6. 6
   その他is purified by flash chromatography on silica gel [eluant: dichloromethane/ethyl acetate (100/0 to 95/5 by volume) gradient]

実験手順

0.214 g of 4-fluorophenylsulfonyl chloride and 0.28 cm3 of triethylamine are added, at room temperature under an argon atmosphere, to a solution of 0.307 g of 1-[bis(4-chlorophenyl)methyl]azetidin-3-ylamine in 10 cm3 of dichloromethane. After stirring for 16 hours at room temperature, the reaction mixture is washed with 10 cm3 of distilled water, 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/ethyl acetate (100/0 to 95/5 by volume) gradient]. 0.18 g of N-{1-[bis(4-chloro-phenyl)methyl]azetidin-3-yl}-4-fluorophenylsulfonamide is obtained in the form of a white foam [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): 2.74 (broad t, J=7.5 Hz: 2H); 2.39 (broad t, J=7.5 Hz: 2H); 3.98 (mt: 1H); 4.20 (s: 1H); 4.79 (d, J=9 Hz: 1H); from 7.10 to 7.35 (mt: 10H); 7.86 (mt: 2H)].

出典