Delta-Valerolactone → HCID 178520562, compound

Participants

Reaction Steps

4-Trifluoromethyl-1,2-phenylenediamine (3 g, 17.03 mmol) and delta-valerolactone (1.78 ml, 18.74 mmol) in 4M HCl (15 ml) were heated to 110° C. for 18 h. The reaction mixture was quenched by addition to sat. NaHCO3(aq) (100 ml), and the mixture was extracted with EtOAc (3×100 ml). The combined organics were dried (MgSO4) and concentrated to afford a brown oil which was triturated with Et2O to afford 3.4 g (77.3%) of 4-(5-Trifluoromethyl-1H-benzoimidazol-2-yl)-butan-1-ol as a tan powder. MS (ESI+) for C12H13F3N2O m/z 258.95 [M+H]+; HPLC ret. time, 1.22 min. 1H NMR (500 MHz, MeOD) δ ppm 7.82 (1H, br. s.), 7.66 (1H, br. s.), 7.44-7.55 (1H, m), 3.62 (2H, t, J=6.46 Hz), 2.99 (2H, t, J=7.65 Hz), 1.89-2.00 (2H, m), 1.58-1.68 (2H, m).

Provenance & Evidence