Hydrochloric Acid → HCID 178481691, compound

Participants

Reaction Steps

2-Furoyl chloride (0.76 ml, 7.66 mmol) was added in a dropwise manner to a solution of 4-methyl-3-thiosemicarbazide (732 mg, 6.96 mmol) and pyridine (7 ml) and the resulting solution was stirred at room temperature for 4 h. The reaction mixture was diluted with ethyl acetate (100 ml), successively washed with water (3×100 ml) and brine (100 ml). The organic phase was dried (sodium sulfate), filtered and concentrated in-vacuo. The residue was suspended in sodium bicarbonate (70 ml, 69.6 mmol, 1 M water) and left stirring at 100° C. overnight. The reaction mixture was cooled to 0° C., then brought to pH about 6 using hydrochloric acid (70 ml, 1 N water). The title compound (298 mg) was collected by filtration as a white solid. 1H NMR (CDCl3), δ (ppm): 11.4 (bs, 1H), 7.63 (d, 1H), 7.02 (d, 1H), 6.60 (dd, 1H), 3.83 (s, 3H).

Provenance & Evidence