反応 #1483054

反応方程式

tetrachloro-1,4-benzoquinone

4-Aminobenzamidine dihydrochloride

formamidine acetate

hydrazine

→

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

収率 19.1%

溶媒

acetonitrile

反応条件

後処理

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

実験手順

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.

出典