2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → HCID 57756899, compound

Participants

Reaction Conditions

Reaction Steps

To 0.055 g (0.233 mmol) of 5-chloro-3-(4-aminophenyl)-1H-pyrrole-2-carboxamide dissolved in 5 cm3 of tetrahydrofuran is added, at a temperature in the region of 20° C. under an argon atmosphere, 0.035 cm3 (0.245 mmol) of 2-fluoro-5-trifluoromethylphenyl isocyanate. After stirring for 2 hours at a temperature in the region of 20° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue, which is recrystallized from 4 cm3 of acetonitrile. After filtering through a No. 3 sinter funnel, the solid is washed with 2 cm3 of acetonitrile and then dried under reduced pressure (2.7 kPa) at a temperature in the region of 35° C. for 4 hours to give 0.076 g of 5-chloro-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]-phenyl}-1H-pyrrole-2-carboxamide in the form of a yellow solid; 1H NMR (400 MHz, DMSO d6, δ in ppm): 6.16 (s, 1H); 6.45 (broad m, 1H); 7.12 (broad m, 1H); 7.38 (partially masked m, 1H); 7.40 (d, J=9.0 Hz, 2H); 7.45 (d, J=9.0 Hz, 2H); 7.49 (dd, J=9.0 and 11.0 Hz, 1H); 8.63 (dd, J=2.0 and 7.5 Hz, 1H); 8.90 (d, J=2.5 Hz, 1H); 9.22 (s, 1H); 12.1 (broad m, 1H); ES+: m/z=291: [M+Na]+.

Provenance & Evidence