反応 #816019

反応方程式

2-[4-(1H-imidazol-1-yl)phenoxy]ethanamine dihydrochloride

sodium hydroxide

N-[4-(oxiranylmethoxy)phenyl]methanesulfonamide

→

title compound

N-[4-[2-Hydroxy-3-[[2-[4-(1H-imidazol-1-yl)phenoxy]ethyl]amino]propoxy]phenyl]methanesulfonamide hydrochloride

溶媒

methanol

water

反応条件

後処理

1. 1
   温度reflux for 16 h
2. 2
   その他Monitor the progress of the reaction by thin-layer chromatography on silica gel (methylene chloride, methanol, triethylamine, 84:15:1)
3. 3
   その他Remove the solvent in vacuo
4. 4
   workup.ADDITIONCombine the fractions containing residue
5. 5
   その他remove the solvent in vacuo
6. 6
   workup.DISSOLUTIONDissolve
7. 7
   workup.ADDITIONin methanol and add a solution of hydrogen chloride in methanol
8. 8
   その他Remove the solvent in vacuo
9. 9
   その他Recrystallize the salt from acetonitrile

実験手順

To a solution of 2.3 g (0.008 mol) of 2-[4-(1H-imidazol-1-yl)phenoxy]ethanamine dihydrochloride in 100 ml of methanol add a solution of 0.66 g of sodium hydroxide in 5 mL of water. Stir for 15 minutes. Add 2.0 g (0.008 mol) of N-[4-(oxiranylmethoxy)phenyl]methanesulfonamide and reflux for 16 h. Monitor the progress of the reaction by thin-layer chromatography on silica gel (methylene chloride, methanol, triethylamine, 84:15:1). Remove the solvent in vacuo. Chromatograph the oil on 350 g of silica gel using amixture of methylene chloride:methanol:triethylamine (94:5:1). Combine the fractions containing residue and remove the solvent in vacuo. Dissolve theresidue in methanol and add a solution of hydrogen chloride in methanol. Remove the solvent in vacuo. Recrystallize the salt from acetonitrile:methanol to obtain the title compound.

出典