Phenyl Isothiocyanate → HCID 25235946, compound

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 phenyl isothiocyanate (97 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 suspend the resulting residue in 1 N NaOH (5 mL). Collect the solid and wash with water. Take the solid up in boiling toluene/EtOAc. Allow to cool. Collect the solid, wash with Et2O, and dry in a vac-oven to afford the title compound as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.03 (t, J=7.39 Hz, 1H) 7.39 (t, J=7.96 Hz, 2H) 7.63-7.69 (m, 3H) 7.71 (d, J=1.26 Hz, 1H) 7.73 (t, J=1.89 Hz, 1H) 7.77 (tautomer A, d, J=8.59 Hz, 1H) 7.83 (tautomer B. dd, J=8.46, 1.52 Hz, 1H) 7.91 (dd, J=8.46, 1.52 Hz, 1H) 8.05 (tautomer B. d, J=1.01 Hz, 1H) 8.17 (tautomer A, s, 1H) 10.68 (s, 1H) 13.30 (d, J=4.17 Hz, 1H); MS (m/z)=422.0 (M+1).

Provenance & Evidence