反应详情

N-Methoxy-N-methyl-3-(pentafluorosulfanyl)-5-(2,2,2-trifluoroacetylamino)benzamide (O4.075; 1.65 g) was dissolved in THF (25 ml). At 0° C., lithium bis(trimethylsilyl)amide (0.9 ml) was added while stirring. After 30 min, methylmagnesium bromide (3.5 ml, 3 M in diethyl ether) was added dropwise. After the addition had ended, the ice bath was removed and the mixture was stirred at RT for 2 h. While cooling, 1 N hydrochloric acid, water and EA were then added. After removing the organic phase, the aqueous phase was extracted twice more with EA. The combined EA phases were dried with magnesium sulfate, filtered and concentrated. The crude product is a mixture of N-(3-acetyl-5-pentafluorosulfanyl-phenyl)-2,2,2-trifluoroacetamide and 1-[3-amino-5-(pentafluorosulfanyl)phenyl]ethanone, and so the crude product (1.3 g) was taken up in methylene chloride (60 ml) and admixed with triethylamine (155 μl). Thereafter, trifluoroacetic anhydride (160 μl) was added while stirring. After stirring at RT for 3 h, water and saturated sodium hydrogencarbonate solution were added, the phases were separated and the DCM phase was washed three times more with water. The DCM phase was dried with magnesium sulfate, filtered and concentrated. 1.3 g of the title compound were obtained.

1. additionAfter the addition
2. customthe ice bath was removed
3. stirringthe mixture was stirred at RT for 2 h
4. temperatureWhile cooling
5. addition1 N hydrochloric acid, water and EA were then added
6. customAfter removing the organic phase
7. extractionthe aqueous phase was extracted twice more with EA
8. dry with materialThe combined EA phases were dried with magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. additiona mixture of N-(3-acetyl-5-pentafluorosulfanyl-phenyl)-2,2,2-trifluoroacetamide and 1-[3-amino-5-(pentafluorosulfanyl)phenyl]ethanone
12. additionThereafter, trifluoroacetic anhydride (160 μl) was added
13. stirringwhile stirring
14. stirringAfter stirring at RT for 3 h
15. additionwater and saturated sodium hydrogencarbonate solution were added
16. customthe phases were separated
17. washthe DCM phase was washed three times more with water
18. dry with materialThe DCM phase was dried with magnesium sulfate
19. filtrationfiltered
20. concentrationconcentrated