Water → N-[3-Fluoro-4-(phenylsulfonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2methylpropanamide

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro2-hydroxy-2-methylpropanoic acid (0.71 g, 4.5 mmol) in N,N-dimethylacetamide (10 mL) was added thionyl chloride (0.54 g, 4.5 mmol) and the mixture stirred at -10° to -15° C. for 1 hour. 3-Fluoro-4-(phenyl sulfonyl)benzeneamine (0.75 g, 3.0 mmol) was added in one portion and the reaction mixture stirred at room temperature overnight. The mixture was poured into water and the aqueous solution filtered through Celite. The Celite was washed with methylene chloride (75 mL), the organic extract dried (MgSO4) and concentrated in vacuo to a tan solid. Purification by flash column chromatography (5% v/v ethyl acetate/methylene chloride) yielded the title propanamide as a white solid (0.79 g, 68%); mp 147°-149° C. 1H--NMR (250 MHz, d6--DMSO): 1.58 (s, 3H, CH3) 7.65-7.69 (m, 4 H, aromatic+OH) 7.74 (d, 1H, J=7.2 Hz, aromatic) 7.83-7.94 (m, 3H, aromatic) 8.02 (t, 1H, J=8.3 Hz, aromatic) 10.61 (s, 1H, NH). MS (CI, CH4): 392 (M+1).

1. stirringthe reaction mixture stirred at room temperature overnight
2. filtrationthe aqueous solution filtered through Celite
3. washThe Celite was washed with methylene chloride (75 mL)
4. extractionthe organic extract
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo to a tan solid
7. customPurification by flash column chromatography (5% v/v ethyl acetate/methylene chloride)

ORD record

ord-b62f8f0dc0d147d0a378cc309736695c

Source dataset

uspto-grants-1993_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05272163