Water → 3-nitro-N-(1,3-thiazol-2-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-aminothiazole (1 g, 10.5 mmol) in dry pyridine (3 ml) was added, portionwise, 3-nitrobenzenesulphonyl chloride (2.32 g, 10.5 mmol), maintaining the internal temperature below 55° C. After addition was complete, the mixture was heated at 100° C. for 75 min. 4M Sodium hydroxide solution (2.75 ml, 11 mmol) was then added dropwise and heating was continued for a further 5 min. After cooling, water (25 ml) was added and the precipitate was collected by filtration to afford the product (2.48 g, 87%) as a brown solid. mp 195° C. (dec.). 1H NMR (360 MHz, D6 -DMSO) δ 6.91 (1H, d, J=4.6 Hz), 7.31 (1H, d, J=4.5 Hz), 7.86 (1H, dd, J=8.0 and 8.1 Hz), 8.20-8.26 (1H, m), 8.40-8.45 ( 1H, m), 8.46-8.49 (1H, m), 13.00 (1H, brs).

Provenance & Evidence