Benzoyl isothiocyanate → 1-(((Benzoylamino)thioxomethyl)amino)-1H-pyrrole-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of benzoylisothiocyanate (1.2 mL, 8.8 mmol) in acetone (10 mL) was treated with 1-aminopyrrole-2-carboxamide (1.0 g, 8.0 mmol) at ambient temperature. The resulting suspension was stirred for one hour and then cooled to 0° C. The solid material was collected by vacuum filtration and washed with diethyl ether before drying under high vacuum to afford 1A (2.2 g, 96%). HPLC tR=2.55 min (YMC S5 Combiscreen ODS 4.6×50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm). [M+H]+=289.29. 1H NMR (400 MHz, DMSO-d6) δ 12.9 (s, 1H), 11.9 (s, 1H), 8.0 (dd, 2H, J=1.2, 7.2 Hz), 7.68 (t, 1H, J=7.6 Hz), 7.55 (m, 3H), 7.03 (s, 1H), 6.92 (br s, 1H), 6.82 (dd, 1H, J=1.6, 4.0 Hz), 6.11 (dd, 1H, J=3.2, 4.0 Hz).

Provenance & Evidence