Dimethyl Sulfoxide → HCID 178502854, compound

Participants

Reaction Conditions

Reaction Steps

1 M aqueous NaOH solution (20 mL) was added to a stirred solution of 178 (1.70 g, 5.5 mmol) in DMSO (20 mL). The mixture was cooled and dimethyl sulfate (1.5 mL, 15.9 mmol) was added dropwise at 0° C. The mixture was stirred at 0° C. for 4 hours and then overnight at room temperature, diluted with water (100 mL). The product was separated as a white solid and purified by column chromatography (SiO2, EtOAc, Hexanes) and recrystallized from aq HCl to give 0.4 g (22%): mp 270-271° C. (dec). 1H NMR (DMSO-d6) δ7.96 (s, 1H), 7.94 (d, J=8.2 Hz, 2H), 7.80 (d, J=8.2 Hz, 2H), 7.64 (s, 2H), 7.55 (s, 2H), 6.16 (br, 2H), 6.13 (br, 2H), 3.77 (s, 3H), 3.76 (s, 3H). HPLC (method A) tR 9.41 min (100.0 area %). Anal. (C18H18N4O3.2HCl) C, H, N, Cl.

Provenance & Evidence