Trimethylamine → (3-Hexadecylsulfanyl-2-methoxy-propyl)-trimethyl-ammonium

Participants

Reaction Steps

To a 100 milliliter heavy wall glass tube equipped with a magnetic stir bar, was added a solution of 2.0 grams (0.005 mole) of (±)-1-hexadecylthio-2-methoxy-3-bromopropane dissolved in 50 milliliters of CH3CN and the vessel was cooled to -10° Centigrade. An excess of condensed trimethylamine was added, the tube was sealed, and the vessel was heated to 60° Centigrade for 24 hours. The reaction mixture was then cooled to room temperature, resulting in a precipitate which was filtered. The precipitate was swirled with five 50 milliliter portions of ether, the ether decanted off, and dried under vacuum, resulting in 2.1 grams (92%) of pure product, (mp 197°-199° Centigrade). 1H-NMR (CDCl3): delta, 0.87(t, 3H, terminal methyl), 1.2-1.6[m, 28H, (CH2)14 ], 2.45-3.0(m, 4H, CH2S--CH2), 3.48[s, 12H, CH3 --O, N(CH3)3 ], 3.5-4.0(m, 3H, CH--CH2N). Anal. (C23H50NOSBr) C,H,N.

Provenance & Evidence