Triethylamine → 2-Methanesulfonyloxyethyl disulfide

Participants

Reaction Steps

10 g of 2,2′-dithiodiethanol and 14.44 g of triethylamine (TEA) are diluted in 100 ml of EtOAc. At 0° C., 16.35 g of methanesulphonyl chloride diluted in 35 ml of EtOAc are added dropwise to the reaction medium with rapid stirring. 7.22 g of TEA are introduced, and the stirring is continued at ambient temperature for 4 h 30. 8.2 g of methanesulphonyl chloride are added dropwise at 15° C., and then the stirring is maintained at ambient temperature for 17 h. The precipitate is filtered off and washed with 3 times 50 ml of EtOAc. The organic phases are extracted with 100 ml of ice-cold water, 100 ml of water, with 3 times 50 ml of a saturated solution of NaHCO3 and with twice 20 ml of saturated NaCl, and are then dried over anhydrous Na2SO4. The EtOAc is evaporated off, and 17.49 g of pale yellow translucent oil are recovered. The analyses indicate that the product is in conformity.

Provenance & Evidence