Study on the Facile Preparation of S-2-(${\omega}$-aminoalkylamino) ethyl Dihydrogen Phosphorothioates

티오인산이수소 S-2-(${\omega}$-아미노알킬아미노) 에틸들의 간편합성법 연구

  • You Sun Kim (Reactor Chemistry Laboratory, Korea Advanced Energy Research Institute) ;
  • Suc Won Kim (Reactor Chemistry Laboratory, Korea Advanced Energy Research Institute)
  • 김유선 (한국에너지연구소 원자로화학연구실) ;
  • 김석원 (한국에너지연구소 원자로화학연구실)
  • Published : 1983.12.20


The facile route of preparing S-2-(${\omega}$-aminoalkylamino) ethyl dihydrogen phosphorothioates, potential chemical radioprotectants, have been studied. Intermediate 3-(2-phthalimidoethyl)-2-oxazolidinone was prepared by a reaction of potassium phthalimide and 3-(2-bromoethyl)-2-oxazolidinone, which was obtained through the alkaline ring closure of a mixture of carbonate and 2,2'-dibromo diethylamine prepared from diethanolamine. This was converted to N-[2-(2-bromoethylamino)ethyl] phthalimide hydrobromide by 30% HBr(gas) in acetic acid and N-(2-bromoethyl)-1,2-ethanediamine dihydrobromide was obtained by reacting the hydrobromide with a solution of HBr-HOAc. N-(2-bromoethyl)-1,3-propanediamine dihydrobromide could be prepared through the Cortese treatment of 2-(3-aminopropylamino) ethanol, which was prepared by a reaction of 1,3-diaminopropane and 2-chloroethanol. These dihydrobromides were treated by sodium thiophosphate in DMF to result S-2-(${\omega}$-aminoalkylamino) ethyl dihydrogen phosphorothioates. The characteristics of each reaction path were discussed in regards to reaction conditions and overall yields and a facile route of preparing each derivative was proposed.



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