3-Nitrobenzenesulfonyl chloride → HCID 19203800, compound

Participants

Reaction Steps

To a stirred suspension of 2-amino-1,3,4-thiadiazole (1.5 g, 15 mmol) in anhydrous pyridine (6 ml) at 0° C., under nitrogen, was added 3-nitrobenzenesulphonyl chloride (3.5 g, 16 mmol) portionwise. The mixture turned yellow and set solid. The mixture was then heated at 120° C. for 1 h before aqueous sodium hydroxide (20% (w/w), 3.3 ml) was added cautiously. Heating was continued for a further 15 min then the solution allowed to cool to ambient temperature. The mixture was evaporated in vacuo and the residue evaporated with water (2×50 ml) followed by toluene (2×50 ml). The residue was then taken up in water and the resultant brown solid collected by filtration. This was then recrystallised from glacial acetic acid. The title compound (1.4 g, 37%) was isolated as a yellow solid, which contained one mole of acetic acid. mp 189°-192° C. 1H NMR (250 MHz, D6 -DMSO) δ 7.88 (1H, dd, J=8 and 8 Hz), 8.23 (1H, dd, J=8 and 1 Hz), 8.45 (2H, m), 8.83 (1H, s).

Provenance & Evidence