Ethylenediamine → 6-[(2-Aminoethyl)amino]pyridine-3-carbonitrile
反応式
[CH:1]1[C:6]([C:7]#[N:8])=[CH:5][N:4]=[C:3](Cl)[CH:2]=1.[CH2:10]([NH2:13])[CH2:11][NH2:12]>>[NH2:12][CH2:11][CH2:10][NH:13][C:3]1[N:4]=[CH:5][C:6]([C:7]#[N:8])=[CH:1][CH:2]=1参加物
3
反応条件
- 温度
- 50 °C
実験手順
6-Chloronicotinitrile (2.0 g) was treated with ethylenediamine (5 ml). The mixture was then heated at 50° C. for 22 hours. Excess ethylenediamine was removed by rotary evaporation. The residue was partitioned between 2.5 M aqueous sodium hydroxide and dichloromethane. The aqueous layer was extracted 4× more with dichloromethane. The combined organic layers were washed with a saturated sodium chloride solution, dried and then concentrated in vacuo to give 6-[(2-aminoethyl)amino]pyridine-3-carbonitrile as an amber liquid which solidified upon standing. The amine (0.97 g, 6 mmol) was shaken overnight with benzotriazole carboxamidinium 4-methylbenzenesulfonate (2.0 g, 6 mmol) and DIEA (1.05 ml, 6 mmol) in acetonitrile (10 ml). Addition of ether gave amino{2-[(5-cyano(2-pyridyl)amino]ethyl}carboxamidinium 4-methylbenzenesulfonate as a white solid.