1,2-Dibromoethane → Allyl-methyl-(2-tritylsulfanyl-ethyl)-amine

Participants

Reaction Steps

5.53 g (20 mmol) triphenylmethanethiol in 50 ml DMA were deprotonated at 0° C. with 0.87 g (20 mmol) of 55% NaH. The reaction was stirred for 30 min at RT, dropped slowly (30 min) to a cooled (0° C.) solution of 1.72 ml (20 mmol) of 1,2-dibromoethane in 50 ml DMA. The reaction mixture was stirred for 6 h at RT, cooled (0° C.) and treated with 3.83 ml (40 mmol) of N-allylmethylamine. After 16 h at RT, the reaction was cooled (0° C.) and treated again with 3.83 ml (40 mmol) of N-allylmethylamine. After 24 h at RT, the solution was concentrated and dissolved in aqueous saturated NaHCO3/Et2O (3×). The organic phase was dried over Na2SO4 and evaporated. Flash column chromatography on silica gel with CH2Cl2/MeOH (99.5:0.5 to 95:5) yielded 3.27 (44%) of Allyl-methyl-(2-tritylsulfanyl-ethyl)-amine, MS: 374 (MH+).

Provenance & Evidence