a. 14.66g (0.142mol) of diethylenetriamine and 2 equivalents (0.284 mol, 39.25g) of K2CO3 were stirred in 200 ml CH3CN in an EtOH/ice bath at -5 oC under N2. b. 0.142 mol (22.29g) of 50% chloroacetaldehyde solution in H2O is mixed with 100ml CH3CN and added dropwise under N2 to the stirring diethylenetriamine. c. Stir under N2 for 6 hours—stirring must be vigorous because of all solid K2CO3. Allow EtOH/ice bath to melt and warm to room temperature. Solution should be colorless with white suspended K2CO3 solid. Reaction can be left stirring overnight under N2. d. Filter white/clear suspension into tared roundbottom flask on disposable frit to remove K2CO3. e. Rotovap to almost clear oil, which might be slightly yellow. Dry on vac line for 1 hr. f. Stir in 160ml diethyl ether until all oil is dissolved. May be some insoluble polymer materials that will not dissolve. g. Filter through celite. Filtrate may be cloudy/white—this appears to be precipitating product due to evaporation and cooling of ether. h. Rotovap to clear oil. Dry on vac line overnight. g. Yield = 13.429g. Theoretical yield = 18.061g. %Yield = 74%. Good elemental and mass spectrum.
a. 14.66g (0.142mol) of diethylenetriamine and 2 equivalents (0.284 mol, 39.25g) of K2CO3 were stirred in 200 ml CH3CN in an EtOH/ice bath at -5 oC under N2. b. 0.142 mol (22.29g) of 50% chloroacetaldehyde solution in H2O is mixed with 100ml CH3CN and added dropwise under N2 to the stirring diethylenetriamine. c. Stir under N2 for 6 hours—stirring must be vigorous because of all solid K2CO3. Allow EtOH/ice bath to melt and warm to room temperature. Solution should be colorless with white suspended K2CO3 solid. Reaction can be left stirring overnight under N2. d. Filter white/clear suspension into tared roundbottom flask on disposable frit to remove K2CO3. e. Rotovap to almost clear oil, which might be slightly yellow. Dry on vac line for 1 hr. f. Stir in 160ml diethyl ether until all oil is dissolved. May be some insoluble polymer materials that will not dissolve. g. Filter through celite. Filtrate may be cloudy/white—this appears to be precipitating product due to evaporation and cooling of ether. h. Rotovap to clear oil. Dry on vac line overnight. g. Yield = 13.429g. Theoretical yield = 18.061g. %Yield = 74%. Good elemental and mass spectrum.
Faith%20Okarocha%20Spring-Summer%202017.docx