반응 #972758

반응 방정식

Ethyl 2-bromo-2-methylpropanoate

5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol

potassium iodide

→

ethyl 2-(5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)-2-methylpropanoate

수율 27.3%

용매

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   온도The temperature was then increased to 90° C.
3. 3
   온도the mixture heated for an additional 6 days
4. 4
   온도to cool to room temperature
5. 5
   농축concentrated
6. 6
   workup.DISSOLUTIONdissolved in dichloromethane
7. 7
   workup.ADDITIONTriethylamine and water were added
8. 8
   기타the layers separated
9. 9
   추출The aqueous layer was extracted with dichloromethane (2×)
10. 10
    건조the combined organic extracts dried over NaSO4
11. 11
    여과filtered
12. 12
    농축concentrated
13. 13
    기타purified by column chromatography (ethyl acetate)

실험 절차

Ethyl 2-bromo-2-methylpropanoate (184 μL, 1.239 mmol) was added to a solution of 5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol (0.35 g, 1.239 mmol) in DMF (2.5 mL) and heated at 60° C. for 20 hours after which time a few crystals of potassium iodide were added and the mixture heated at 70° C. for a further 24 h. The temperature was then increased to 90° C. and the mixture heated for an additional 6 days. The mixture was allowed to cool to room temperature, concentrated and dissolved in dichloromethane. Triethylamine and water were added and the layers separated. The aqueous layer was extracted with dichloromethane (2×) and the combined organic extracts dried over NaSO4, filtered, concentrated and purified by column chromatography (ethyl acetate) to afford ethyl 2-(5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)-2-methylpropanoate as a tan solid (0.134 g, 27%).

출처