Water → HCID 10644163, compound

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). Analysis for C16H13F4NO4S: Calculated: C, 49.11; H, 3.35; N, 3.58 Found: C, 49.28; H, 3.51; N, 3.66

1. customthe mixture (a precipitate formed after a few minutes)
2. stirringto stir at room temperature overnight
3. customthe cloudy solution decanted from the resulting gum
4. filtrationfiltered through a thin pad of Celite
5. washThe Celite pad was washed with methylene chloride
6. additionthe solution added to a solution of the gum in methylene chloride
7. dry with materialThe combined methylene chloride solution was dried (MgSO4)
8. filtrationfiltered
9. customthe solvent removed in vacuo
10. additionThe resulting gum was treated with hexane (100 mL) and enough methylene chloride (ca. 100 mL)
11. customto yield a solution
12. temperatureThe solution was cooled
13. concentrationconcentrated
14. temperatureAfter cooling the solid
15. filtrationwas filtered

ORD record

ord-813fe06247674128b25705f7a388d449

Source dataset

uspto-grants-1995_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05474999