反应 #1483054

反应方程式

tetrachloro-1,4-benzoquinone

4-Aminobenzamidine dihydrochloride

formamidine acetate

hydrazine

→

4-(1,2,4,5-tetrazin-3-yl)aniline

收率 19.1%

溶剂

acetonitrile

反应条件

后处理

1. 1
   温度The solution was heated
2. 2
   温度to reflux for 1 hour
3. 3
   温度cooled
4. 4
   其他the solvent was removed by rotary evaporation
5. 5
   其他After removal of the solids from the pink solution
6. 6
   过滤by filtration
7. 7
   浓缩the reaction was concentrated by rotary evaporation
8. 8
   其他purified by preparative HPLC

实验过程

To a mixture of 4-Aminobenzamidine dihydrochloride (1 mmol, 208 mg) and formamidine acetate (4 mmol, 416 mg) in acetonitrile (25 mL) was added anhydrous hydrazine (10 mmol, 315 uL). The solution was heated to reflux for 1 hour, cooled, and the solvent was removed by rotary evaporation. The residue was resuspended with water (25 mL) and was stirred with solid tetrachloro-1,4-benzoquinone (2 mmol, 492 mg) for 1 hour. After removal of the solids from the pink solution by filtration, the reaction was concentrated by rotary evaporation and purified by preparative HPLC using a gradient from 0-40% buffer B (buffer A is water with 0.1% TFA, and buffer B is acetonitrile with 10% water and 0.1% TFA) to afford pure 4-(1,2,4,5-tetrazin-3-yl)aniline (33 mg, 19%), as a pink solid. LRMS-ESI [M+H]+ calcd. for C8H8N5+: 174.08, found: 173.9.

来源