反応 #806271

反応方程式

triethylamine

thien-2-ylsulfonyl chloride

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

→

N-{1-[bis(4-chlorophenyl)-methyl]azetidin-3-yl}thien-2-ylsulfonamide

収率 66.2%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   workup.ADDITIONthe reaction mixture is introduced into a Bond Elut® SCX cartridge (3 cm5/500 mg)
2. 2
   洗浄eluting successively with twice 2 cm3 of dichloromethane
3. 3
   濃縮concentrated to dryness under reduced pressure (2.7 kPa)
4. 4
   その他The residue obtained
5. 5
   洗浄washed with three times 3 cm3 of distilled water
6. 6
   乾燥dried over magnesium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated to dryness under reduced pressure (2.7 kPa)

実験手順

69.3 mm3 of triethylamine and 110 mg of thien-2-ylsulfonyl chloride are successively added, at room temperature and under an argon atmosphere, to a solution of 61.4 mg of 1-[bis(4-chlorophenyl)methyl]-azetidin-3-ylamine in 3 cm3 of dichloromethane. After stirring for 68 hours at room temperature, the reaction mixture is introduced into a Bond Elut® SCX cartridge (3 cm5/500 mg), eluting successively with twice 2 cm3 of dichloromethane and then twice 2 cm3 of a 1 M solution of ammonia in methanol. The ammoniacal fractions are pooled and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is dissolved in 5 cm3 of dichloromethane, washed with three times 3 cm3 of distilled water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). 60 mg of N-{1-[bis(4-chlorophenyl)-methyl]azetidin-3-yl}thien-2-ylsulfonamide are thus obtained in the form of a cream-colored foam [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): 2.77 (split t, J=7 and 2 Hz: 2H); 3.40 (split t, J=7 and 2 Hz: 2H); 4.06 (mt: 1H); 4.21 (s: 1H); from 4.85 to 5.25 (broad unresolved complex: 1H); 7.06 (t, J=4.5 Hz: 1H); from 7.15 to 7.35 (mt: 8H); 7.58 (mt: 2H)].

出典