Phosphorus oxychloride → HCID 57687362, compound

Participants

Reaction Steps

Dimethylaniline (0.770 mL, 0.61 mmol) was added to a stirring solution of example 31b (15 g, 66.1 mmol) in POCl3 (36 mL, 397 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 21 h. The reaction was concentrated in vacuo, poured onto ice, and the resulting precipitate was collected by filtration to give 14 g (87%) of clean desired product as a beige solid. The filtrate was extracted with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under reduced pressure to give an additional 2 g (12%) of clean desired product. 1H NMR (400 MHz, DMSO-d6): δ 6.99 (q, 1H, J=4.8 Hz), 5.80 (s, 1H), 4.23 (q, 2H, J=7.2 Hz), 3.32 (s, 3H), 2.76 (d, 3H, J=4.8 Hz), 1.27 (t, 3H, J=7.2 Hz). MS (ES) [m+H] calc'd for C10H13ClN2O3, 245; found 245.

Provenance & Evidence