Unsaturated Sulfones for Treating Proliferative Disorders

Patent a, j8-Unsaturated Sulfones for Treating Proliferative Disorders 

Reddy etal, US Patent 6,599,932 (July 29, 2003) Assignee Temple University of the Commonwealth System of Higher Education 

Thioglycolic acid (0.1 mol) was added to a solution of NaOH (0.2 mol) dissolved in 200 ml methyl alcohol followed by the addition of 4-fluorobenzyl chloride (0.1 mol) and the reaction refluxed 3 hours. The mixture was cooled to ambient temperature, poured onto crushed ice, neutralized with 200 ml HCl, and the product isolated. 

A mixture of the product from Step 1 (0.1 mol), hydrogen peroxide (0.12 mol) in 125 ml HO Ac was refluxed 1 hour, cooled, re-crystallized in water, and the product isolated. 

The product from Step 2 (10 mmol) was mixed with 2-pyridine-carboxaldehyde (10 mmol) and 200 ml benzylamine in 12 ml HO Ac, refluxed 3 hours, cooled, and treated with 50 ml diethyl ether. Any precipitation was removed by filtration. The filtrate was diluted with additional diethyl ether, washed successively with NaHC03, sodium bisulfite, HCl, and 35 ml water. The mixture was concentrated and the product isolated as solid. 

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