Phosphorus oxychloride → HCID 178425403, compound

Participants

Reaction Steps

Phosphoryl Chloride (3.3 mL,3.54 mmol) was added to a solution of 14 (40.2 mg, 0.10 mmol) in DMF (1 ml). Following stirring under N2 for 24 hrs, the cmde product was isolated by diluting with Et2O. The product was then purified by recrystillization from CHCl3Et2O/EtOH. Giving pure compound 15 (31.2 mg, 74%) as an off-white solid: 1H NMR (270 MHz, MeCN d3) δ8.14(d, 1H, I=8.2 Hz, ArNO2), 8.07(d, J=8.2 Hz, 1H, ArNO2), 7.81 (t, J=8.2 Hz, 1H, ArNO2), 7.59(t, J=8.2 Hz, 1H, ArNO2), 7.49(t, J=5.2 Hz, 1H, RCH2NH), 7.19(s, 2H, Ar-H), 5.20.(s, 2H, ArOCH2 Ar(NO2)), 5.04(m, 1H, ArCH(OH)), 3.71(m, 2H, CH2—NH), 2.24(s, 6H, ArCH) 13C NMR (67.5 MHz, MeOHd4) δ157.4, 156.1, 147.4, 134.1, 133.7, 133.4, 131.5, 128.8, 128.5, 127.9, 124.5, 70.1, 60.3, 48.3, 15.2;

Provenance & Evidence