Methanol → HCID 21833796, compound

Participants

Reaction Steps

(4-Bromo-3-methylbenzylidene)methylamine (D91, 2.15 g, 10.1 mmol) was dissolved in dry DME (30 ml) and methanol (70 ml) containing tosylmethylisocyanide (3.0 g; 15.4 mmol) and this solution was treated with potassium carbonate (2.8 g, 20.3 mmol). The whole was heated at reflux for 48 hours, cooled and evaporated in vacuo. The residue was partitioned between brine and chloroform (3 times), and the organics combined and dried over Na2SO4. The organics were filtered and evaporated in vacuo then the residue purified by flash silica gel chromatography (with chloroform as eluant) to yield the title compound as an orange gum (1.52 g, 60%).

Provenance & Evidence