반응 #1483054

반응 방정식

tetrachloro-1,4-benzoquinone

4-Aminobenzamidine dihydrochloride

formamidine acetate

hydrazine

→

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

수율 19.1%

용매

acetonitrile

반응 조건

후처리

1. 1
   온도The solution was heated
2. 2
   온도to reflux for 1 hour
3. 3
   온도cooled
4. 4
   기타the solvent was removed by rotary evaporation
5. 5
   기타After removal of the solids from the pink solution
6. 6
   여과by filtration
7. 7
   농축the reaction was concentrated by rotary evaporation
8. 8
   기타purified by preparative HPLC

실험 절차

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.

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