반응 #587300

반응 방정식

1-(4-bromo-3-fluorophenyl)-2,2-diethoxyethanone

aminoguanidine bicarbonate

potassium hydroxide

→

desired product

6-(4-Bromo-3-fluorophenyl)-1,2,4-triazin-3-amine

용매

ethanol

water

반응 조건

후처리

1. 1
   온도was refluxed overnight
2. 2
   기타The solvent was evaporated under reduced pressure
3. 3
   세척the residue was washed with acetonitrile
4. 4
   여과filtered
5. 5
   농축The filtrate was concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (100 mL)
7. 7
   세척washed with water, brine
8. 8
   농축concentrated under reduced pressure
9. 9
   workup.DISSOLUTIONThe residue was dissolved in ethanol (50 mL)
10. 10
    workup.ADDITIONTo the solution was added 0.2N hydrochloric acid (50 mL)
11. 11
    온도cooled with an ice-water bath
12. 12
    기타The precipitate that formed
13. 13
    여과was collected by filtration
14. 14
    세척washed with isopropanol

실험 절차

A mixture of 1-(4-bromo-3-fluorophenyl)-2,2-diethoxyethanone (15.2 g, 50 mmol), aminoguanidine bicarbonate (10.2 g, 75 mmol) and potassium hydroxide (6.6 g, 100 mmol) in ethanol (200 mL) and water (4 mL) was refluxed overnight. The solvent was evaporated under reduced pressure and the residue was washed with acetonitrile and filtered. The filtrate was concentrated under reduced pressure. The residue was dissolved in dichloromethane (100 mL), washed with water, brine, and concentrated under reduced pressure. The residue was dissolved in ethanol (50 mL). To the solution was added 0.2N hydrochloric acid (50 mL). The resultant mixture was heated to 110° C. for 8 h, and cooled with an ice-water bath. The precipitate that formed was collected by filtration and washed with isopropanol to give the desired product. (5.5 g, 41%) LCMS: (M+H)=286.8/288.8. 1H-NMR (400 MHz, CDCl3): 8.60 (s, 1H), 7.79 (dd, J=8.6, 2.0 Hz, 1H), 7.68 (dd, J=8.3, 7.0 Hz, 1H), 7.61 (dd, J=8.3, 2.0 Hz, 1H), 5.43 (s, 2H).

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