Hydrochloric Acid → HCID 178434363, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (E)-1-(diphenylmethylene)-2-(1-(3-(2-(diphenylmethylene)hydrazinyl)thiophen-2-yl)ethylidene)hydrazine (12.5 g, 25.07 mmol) in EtOH (75 mL) was added concentrated HCl (40 mL). The reaction mixture was heated at 80° C. for 2 hours, then basified with saturated aqueous NaHCO3 (50 mL) and solid NaHCO3 to pH 8-9. The reaction mixture was extracted with EtOAc (2×250 mL). The organic layers were combined, dried over sodium sulfate, and evaporated. The resulting mixture was purified by silica gel column chromatography, eluting with a gradient of 0-20% dichloromethane and methanol. The pure product fractions were combined and evaporated to give the title compound as a tan solid (2.6 g, 75%). 1H NMR (400 MHz, CDCl3) δ ppm 2.42-2.57 (m, 3H), 6.97 (d, J=5.05 Hz, 1H), 7.40 (d, J=5.31 Hz, 1H), 9.04 (br s, 1H). ESI-MS m/z [M+H]+ calc'd for C6H6N2S, 139. found, 139.

Provenance & Evidence