反応 #414339

反応方程式

water

thionyl chloride

3,3,3-trifluoro-2-hydroxy-2-methyl propanoic acid

4-(2-Fluorophenylsulfonyl)benzenamine

→

propanamide

収率 82.0%

N-[4-(2-Fluorophenylsulfonyl)phenyl]-3,3,3,-trifluoro-2-hydroxy-2-methyl propanamide

収率 82.0%

溶媒

Methylene chloride

N,N-dimethylacetamide

反応条件

後処理

1. 1
   その他the mixture (a precipitate formed after a few minutes)
2. 2
   workup.STIRRINGto stir at room temperature overnight
3. 3
   その他the cloudy solution decanted from the resulting gum
4. 4
   ろ過filtered through a thin pad of Celite
5. 5
   洗浄The Celite pad was washed with methylene chloride
6. 6
   workup.ADDITIONthe solution added to a solution of the gum in methylene chloride
7. 7
   乾燥The combined methylene chloride solution was dried (MgSO4)
8. 8
   ろ過filtered
9. 9
   その他the solvent removed in vacuo
10. 10
    workup.ADDITIONThe resulting gum was treated with hexane (100 mL) and enough methylene chloride (ca. 100 mL)
11. 11
    その他to yield a solution
12. 12
    温度The solution was cooled
13. 13
    濃縮concentrated
14. 14
    温度After cooling the solid
15. 15
    ろ過was filtered

実験手順

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methyl propanoic acid (1.42 g 9.0 mmol) in N,N-dimethylacetamide (13 mL) was rapidly added thionyl chloride (1.13 g, 9.5 mmol) and the mixture (a precipitate formed after a few minutes) stirred at -15° to -5° C. for 1 hour. 4-(2-Fluorophenylsulfonyl)benzenamine (1.51 g, 6.0 mmol) was then added in one portion and the mixture allowed to stir at room temperature overnight. The solution was poured into water, the cloudy solution decanted from the resulting gum and filtered through a thin pad of Celite. The Celite pad was washed with methylene chloride and the solution added to a solution of the gum in methylene chloride. The combined methylene chloride solution was dried (MgSO4), filtered and the solvent removed in vacuo. The resulting gum was treated with hexane (100 mL) and enough methylene chloride (ca. 100 mL) to yield a solution. Methylene chloride was then boiled off on a steam bath at atmospheric pressure until cloudiness developed. The solution was cooled and scratched with a spatula until crystal growth began, returned to the steam bath and concentrated with swirling until the final volume was 100 mL. After cooling the solid was filtered to yield the title propanamide (1.92 g, 82%) as a light tan solid; mp 124°-133° C. 1H--NMR (400 MHz, d6 --DMSO): 1.59 (s, 3H, CH3), 7.41 (t, 1H, aromatic), 7.51 (t, 1H, aromatic), 7.59 (s, 1H, OH), 7.77 (m, 1H, aromatic), 7.85 (d, 2H, J=8.7 Hz, aromatic), 7.98-8.06 (m, 3H, aromatic), 10.48 (s, 1H, NH). MS (CI, CH4): 392(M+1).

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