3-Chloro-2-chloromethyl-1-propene → HCID 465407, compound

Participants

Reaction Steps

In a 500 mL three-necked round-bottomed flask equipped with a rubber septum and a gas inlet, 0.92 g of a 60% (w/w) dispersion of sodium hydride in mineral oil (0.55 g NaH, 23 mmol) was washed with hexane (3×15 mL) under N2. A solution of 5.78 g (11.5 mmol) of N-benzylbis(3-benzenesulfonamidopropyl)amine in 220 mL of DMF was added slowly with stirring. The resulting clear solution was stirred under N2 while a solution of 1.44 g (11.5 mmol) of 3-chloro-2-chloromethyl-l-propene in 8 mL of DMF was added dropwise over 10 h. Stirring at room temperature under N2 was continued for an additional 24 h. The solvent was removed by rotary evaporation evaporation using a hot water bath. A solution of the residue in 50 mL of CHCl3 was washed with water (3×30 mL) and saturated aq. NaCl (2×30 mL) then dried (MgSO4). Removal of the drying agent by filtration and concentration of the filtrate by rotary evaporation gave the crude product as a thick yellow oil. The oil was dissolved in 100 mL of 1:1 (v/v) ethyl acetate/hexane and filtered through a pad of 16 g of basic alumina (Act 1, 80-200 mesh) washing with an additional 50 mL of 1:1 ethyl acetate/hexane. Concentration of the combined filtrates under vacuum afforded 4.93 g (77 %) of 9-benzyl-3-methylene-1,5-dibenzenesulfonyl-1,5,9-triazacyclododecane as a bubbly film that was converted to the hydrochloride salt.

Provenance & Evidence