4-Aminobenzophenone → N-[4-(Phenylcarbonyl)phenyl]-3,3-difluoro-2-hydroxy-2-difluoromethylpropanamide

To a solution of 2,2,-bis-difluoromethyl-2-hydroxy-acetic acid (1.76 g, 10 mmole) in tetrahydrofuran (40ml) was added carbonyl diimidazole (0.81 g, 5 mmole). The flask was placed in a sonic bath and the reaction sonicated for 20 minutes followed by addition of 4-aminobenzophenone. The reaction was sonicated for 18 hours. The reaction mixture was filtered and the filtrate evaporated to dryness. The recovered pasty solid was washed with ether and the combined ether washings evaporated. The recovered solid was crystallized from ethyl acetate/hexane to give the title compound (0.89g, 25%) as yellow crystals; mp 139°-142° C. 1H--NMR (300 MHz, d6 --DMSO) : 6.48(t, J=53.7Hz, 2H, HCF2); 7.53-7.77 7H, ArH, OH); 7.95-7.98(m, 3H, ArH); 10.43 (s, 1H, NH). MS(CI,CH4) 356(M+1, 100%).

1. customThe flask was placed in a sonic bath
2. customthe reaction sonicated for 20 minutes
3. customThe reaction was sonicated for 18 hours
4. filtrationThe reaction mixture was filtered
5. customthe filtrate evaporated to dryness
6. washThe recovered pasty solid was washed with ether
7. customthe combined ether washings evaporated
8. customThe recovered solid was crystallized from ethyl acetate/hexane

ORD record

ord-7477f9b6e0aa4baf820ffd5b0e4f40ca

Source dataset

uspto-grants-1993_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05272163