反応 #944968

反応方程式

KOH

3-[2-(azidomethyl)-4-chlorophenyl]-4-chloro-1,2,5-thiadiazole

water

triphenyl phosphine

→

1-[5-Chloro-2-(4-chloro-1,2,5-thiadiazole-3-yl)phenyl]methanamine

溶媒

THF

MeOH

反応条件

後処理

1. 1
   温度The solution was refluxed 1 h
2. 2
   温度the solution was refluxed 5 min
3. 3
   その他partitioned between 1 M HCl and EtOAc
4. 4
   その他The aqueous phase was separated
5. 5
   抽出extracted into ether
6. 6
   その他The organic phase was separated
7. 7
   乾燥dried (Na2SO4)
8. 8
   その他The residue was purified by flash chromatography on silica (eluting with EtOAc/hexanes gradient, 5–10% EtOAc followed by 0.9% MeOH/0.1% NH4OH/chloroform)

実験手順

To a stirred solution of 3-[2-(azidomethyl)-4-chlorophenyl]-4-chloro-1,2,5-thiadiazole (0.205 g, 0.72 mmol) and water (0.01 mL, 0.72 mmol) in THF (1.5 mL) was added triphenyl phosphine (0.188 g, 0.72 mmol). The solution was refluxed 1 h then stirred at ambient temperature for 16 h. The solution was reduced in vacuo and the residue was dissolved in MeOH. KOH (1 pellet) was added and the solution was refluxed 5 min. The solution was reduced in vacuo and partitioned between 1 M HCl and EtOAc. The aqueous phase was separated, basified with 1 M NaOH and extracted into ether. The organic phase was separated, dried (Na2SO4) and reduced in vacuo. The residue was purified by flash chromatography on silica (eluting with EtOAc/hexanes gradient, 5–10% EtOAc followed by 0.9% MeOH/0.1% NH4OH/chloroform). 1-[5-Chloro-2-(4-chloro-1,2,5-thiadiazole-3-yl)phenyl]methanamine was isolated as a yellow oil. MS m/z=260.5.

出典