asau09

I would have definitely used that approach, but I was trying to alkylate p-toluenesulfonamide with an alkyl group (butyne with an internal C-C triple bond), but we don't have butynyl amine in our lab (if it does exist at all).

I have not, but I will test it out. Thanks for the reply! Just for clarification, how would the MeOH:DCM solvent mixture be different than using Hexane:EtOAc? Would it be because of the polarities of MeOH and DCM versus hexane and ethyl acetate?

Hello fellow scientists, A few days ago, I ran a reaction of an alkynyl tosylate (specifically ROTs, the R group being an internal alkyne) with p-toluenesulfonamide (TsNH2) in base (K2CO3) in hopes of alkylating the sulfonamide, and getting RNHTs out as the product. This reaction took much longer than I imagined, and I finally decided to work it up after 3 days of it running. When I took a TLC test of the crude, there was some starting material, the product spot, and p-toluenesulfonamide. From past experience (I ran this reaction before, except using 1-bromo-2-butyne), I had to use a 1:1 Hexane:EtOAc mixture to chromatograph this mixture, leaving me with ~50% yield of product. Last time, however, I had no starting material left over so chromatographing it was more simple compared to this time. I've been having issues trying to get the solids of the mixture (yes, the substrates and products are all solid) to dissolve in the Hex:EtOAc (4:1) system (this provided a better separation, as seen by TLC). I've tried dry-loading using silica, recrystallization from methanol and hexane, and so far nothing's working!! Please help me figure out how to solve this issue...