Carbon Dioxide → N-[4-(Phenylcarbonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-trifluoromethyl-propanamide

Temperature

23 °C

Tetrahydrofuran (35 ml,dry) was added to a mixture of 2,2-bis-trifluoromethyl 2-hydroxyacetic acid (1.08 g, 5.1 mmol) and 1,1'-carbonyldiimidazole (0.83 g, 5.1 mmol), while under a nitrogen atmosphere. There was an immediate evolution of carbon dioxide. The reaction was refluxed for 0.5 hrs and cooled to 23° C. The reaction was treated with 4-aminobenzophenone (1.0 g,5.1 mmol), stirred at 23° C. for 1.5 hrs, and then at reflux 18 hrs. The reaction was evaporated to a yellow oil-solid mixture. The mixture was dissolved in ethyl ether, treated with hydrogen chloride in ethyl ether, and filtered. The filtrate was evaporated to a yellow oil-solid mixture. Chromatography of this mixture on silica gel, eluting with 5% ethylether in methylenechloride provided the title compound as an off-white solid; mp 143°-146° C. 1H--NMR (250 MHz,d6 --DMSO): 7.67(m, 2H, ArH), 7.83(m, 5H, ArH),7.96(d, J=8.8, 2H, ArH), 9.82(s, 1H, OH), 10.82(s, 1H, NH). MS(CI,CH4): 392 (M+1).

1. temperatureThe reaction was refluxed for 0.5 hrs
2. temperatureat reflux 18 hrs
3. customThe reaction was evaporated to a yellow oil-solid mixture
4. dissolutionThe mixture was dissolved in ethyl ether
5. additiontreated with hydrogen chloride in ethyl ether
6. filtrationfiltered
7. customThe filtrate was evaporated to a yellow oil-solid mixture
8. washChromatography of this mixture on silica gel, eluting with 5% ethylether in methylenechloride

ORD record

ord-03cdd477d3994fc9b2024e6efca8200b

Source dataset

uspto-grants-1993_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05272163