Methyl p-toluenesulfonate → Iodide Ion

Participants

Reaction Steps

The starting 2,3-dimethyl-β-naphthothiazolium tosylate (Compound 7A) is prepared by heating equal moles of the 2-methyl-β-naphthothiazole (Aldrich Chemical Co.) and methyl tosylate at 160° C. for an hour. The tosylate (Compound 7A, 0.385 g, 1 mmoles) is then stirred in 10 mL of methylene chloride at room temperature with 0.41 g (1 mmoles) of 1-(3-iodopropyl)-4-chloropyridinium iodide (from 4-chloropyridine and 1,3-diiodopropane) while 0.14 mL (1 mmoles) of triethylamine is introduced. The reaction mixture is stirred at room temperature overnight and the desired monomer (Compound 7B) is isolated as its iodide salt by filtration. 7B is then dimerized according to Example 1 to yield Compound 7.

Provenance & Evidence