Réaction #1483054

Équation de réaction

tetrachloro-1,4-benzoquinone

4-Aminobenzamidine dihydrochloride

formamidine acetate

hydrazine

→

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

Rendement 19.1%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   TempératureThe solution was heated
2. 2
   Températureto reflux for 1 hour
3. 3
   Températurecooled
4. 4
   Autrethe solvent was removed by rotary evaporation
5. 5
   AutreAfter removal of the solids from the pink solution
6. 6
   Filtrationby filtration
7. 7
   Concentrationthe reaction was concentrated by rotary evaporation
8. 8
   Autrepurified by preparative HPLC

Mode opératoire

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.

Source