Acetic Acid → HCID 18975331, compound

Participants

Reaction Steps

A mixture of Intermediate 5 (1.62 g, 8.7 mmol) and hexamethylenetetramine (1.47 g, 10.5 mmol) was refluxed in 33% aqueous acetic acid (10 mL) for 75 min. The mixture was cooled in ice for 2 hours and the precipitate was collected by filtration to give the title compound (0.71 g, 38%) as a beige solid. The filtrate was evaporated and the residue chromatographed on silica eluting with 10% MeOH in DCM to give the title compound (0.39 g, 21%) (overall yield 59%), as a yellow solid. mp 155° C. (dec.). 1H NMR (360 MHz, d6 -DMSO) δ 8.35 (1H, s), 8.68 (1H, s), 8.83 (1H, s), 9.30 (2H, s), 10.05 (1H, s) and 12.74 (1H, br s).

Provenance & Evidence