Sodium Iodide → 7-Nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine

Participants

Reaction Steps

To a stirred solution of 2-(2-chloroethylthio)-4-nitroaniline (5.13 g, 22.05 mmol) in DMF (70 mL) was added potassium carbonate (9.14 g, 66.1 mmol), followed by sodium iodide (0.330 g, 2.205 mmol). The resulting suspension was stirred at room temperature overnight. The mixture was then diluted with water, and the resulting crystals were collected by vacuum filtration, giving the desired product (4.06 g, 94%). 1H NMR (DMSO-d6) δ 7.81-7.73 (m, 3H), 6.58 (t, J=9.0 Hz, 1H), 3.65-3.60 (m, 2H), 3.01-2.97 (m, 2H); ESI-MS (m/z, %): 197 (MH+, 100), 180 (99).

Provenance & Evidence