So I have a bicyclic 2-sulfonyl pyridine with an CH2- dimethyl amide attached. The reaction appears high yielding by crude NMR but the TLC profile has a more or less a continuous streak of trace impurities all the way up the plate which are only visible by UV. I've tried many different solvent systems and I can't get any resolution. I don't think its my desired compound streaking or anything like that because triethylamine in the eluent didn't help. I'm working on a small scale so I tried multiple elutions on prep TLC after an initial silica plug, but there is still roughly 10 % junk. I'm thinking I should try recrystalization, but since I haven't gotten the stuff pure I don't know if its a solid or not (MW>400). Any ideas on how to approach this? I have plenty of the crude to mess around with, but I don't want to waste my time trying to recrystallize if its an oil in pure form. Thanks!