To a round bottomed flask was added thioxanthen-9-ol (0.5 g, 2.3 mmol), 2-nitroaniline (0.4g, 2.9 mmol), acetic acid (0.25 mL) and ethanol (10 mL)*. The reaction mixture was fitted with a condenser and heated to reflux with constant stirring.**  After two hours at reflux, the solution was allowed to cool to room temperature, a glass stopper fitter and orange mixture transferred to a freezer and left overnight***.  The precipitate produced was isolated under vacuum filtration and washed with cold ethanol to give N-(2-nitrophenyl)-9H-thioxanthen-9-amine (0.16g, 20%) as an orange precipitate.

1H NMR (400 MHz, DMSO-d6) δ 8.76 (d, J = 8.9 Hz, 1H), 8.06 (dd, J = 8.6, 1.6 Hz, 1H), 7.71 – 7.61 (m, 4H), 7.58 – 7.52 (m, 1H), 7.45 (dd, J = 8.9, 1.3 Hz, 1H), 7.37 – 7.32 (m, 4H), 6.74 (ddd, J = 8.4, 6.8, 1.2 Hz, 1H), 6.21 (d, J = 8.8 Hz, 1H).  13C NMR (101 MHz, DMSO) δ 143.40, 136.51, 134.84, 132.03, 131.71, 127.84, 127.68, 127.47, 127.03, 126.44, 116.35, 115.58, 54.87. LC-MS 335 [M+1].

Hori, M., Kataoka, T., Ohno, K., Toyoda, T.; Reactivities of 9-​phenylxanthylium and 9-​phenylthioxanthylium salts in electrophilic and nucleophilic reactions.  I.  Nitration Chemical & Pharmaceutical Bulletin (1973), 21(6), 1272-1281.