Toluene → HCID 9883158, compound

Participants

Reaction Steps

A mixture of 1-(4-fluorophenyl)-3-oxo-1,3-dihydro-2-benzofuran-1-carboxamide (12.5 g) (Step 1 of Example 2), 1,2-diaminopropane (13.5 g), and toluene (150 mL) was heated at reflux for 18 h in a flask equipped with a water separator. The mixture was evaporated to dryness. The residue was treated with hot ethanol (200 mL). The insoluble material was collected by filtration and dried to give the title compound (4.3 g) as a white solid m.p. 229-232° C. Mass spectrum (EI, M+) m/z 310. 1H NMR (400 MHz, DMSO-d6) δ 8.04 (d, 1H), 7.62 (t, 1H), 7.51 (t, 1H), 7.33 (m, 3H), 7.10 (t, 2H), 7.04 (s, 1H), 4.13 (m, 1H), 4.02 (dd, 1H), 3.52 (dd, 1H), and 1.20 ppm (d, 3H).

Provenance & Evidence