تفاعل #1483054

معادلة التفاعل

tetrachloro-1,4-benzoquinone

4-Aminobenzamidine dihydrochloride

formamidine acetate

hydrazine

→

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

المردود 19.1%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe solution was heated
2. 2
   درجة الحرارةto reflux for 1 hour
3. 3
   درجة الحرارةcooled
4. 4
   أخرىthe solvent was removed by rotary evaporation
5. 5
   أخرىAfter removal of the solids from the pink solution
6. 6
   ترشيحby filtration
7. 7
   تركيزthe reaction was concentrated by rotary evaporation
8. 8
   أخرىpurified by preparative HPLC

الإجراء التجريبي

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.

المصدر