S-alkylation of thiols
To a solution of the thiol (0.013 mol) in 140 mL ethanol was added sodium hydroxide (0.039 mol) slowly at room temperature over a period of 5 minutes. Sodium hydroxide was completely dissolved in 30 minutes. Then alkyl chloride (0.014 mol) was added slowly at 0 oC. The resulting mixture was stirred at room temperature for overnight (12 h). White solid precipitated out. The solvent was evaporated, the residue was dissolved in 50 mL water and 250 mL ethyl acetate, extracted, the organic layer was dried (Na2SO4) and evaporated under reduced pressure to give the corresponding S-alkylated product which was purified by triturating with ether (white solid, 90% yield).
