Ethyl Acetate → {5-[2-(2,6-Dichloro-phenyl)-3H-benzoimidazol-5-yl]-[1,3,4]oxadiazol-2-yl}-m-tolyl-amine

Participants

Reaction Steps

To a solution of 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (150 mg, 0.466 mmol) in DMF (3 mL) add m-tolyl isothiocyanate (69 uL, 0.512 mmol) and stir for 3.5 hr. Add EDCI (179 mg, 0.932 mmol) and heat to 80° C. for 1 hr. Upon cooling to room temp dilute the reaction with EtOAc (75 mL) and extract with water (15 mL). Evaporate the organic phase and recrystallize from toluene/EtOAc. Suspend the solid in 1 N NaOH. Collect the solid wash with water and Et2O to afford the title compound as a white solid: 1H NMR (400 MHz, MeOD) ppm 2.38 (s, 3 H) 6.90 (d, J=7.58 Hz, 1 H) 7.26 (t, J=7.77 Hz, 1 H) 7.37 (d, J=1.77 Hz, 1 H) 7.43 (s, 1 H) 7.56-7.65 (m, 3 H) 7.82 (d, J=8.59 Hz, 1 H) 8.01 (dd, J=8.53, 1.33 Hz, 1 H) 8.27 (s, 1H); MS m/z=436.1 (M+1).

Provenance & Evidence