After that fucked up, I got blazed and worked out a series of steps to eventually end up with my product:
acetanilide -->p-nitroacetanilide --> p-aminoacetanilide --> I'm not sure the name of this one, but I'm changing the amino group to an N2 + group --> p-cyanoacetanilide --> using methyl grinard and something else add a methyl group the the C of the cyano and replace the N with an O for the final product
So my professor liked the idea and let me give it a shot. At this point I've definitely made the nitroacetanilide and I'm pretty sure I have my aminoacetanilide from it (I've got to run an IR and mass spec still yet, but the GC showed the reaction went through almost completely). I'm stuck though on the next step. While the organic book gives basic reagents to use for each of the various reactions in this process, I've been using the sci-finder database (scifinder.cas.org) to get specific reaction conditions and reagents for each of the steps so far for journal articles. After looking up the conversion of the amino group to an N2 + group, however, I can't find a specific reaction for the conversion from aminoacetanilide (though I've found reactions for the conversion of the functional group on similar molecules). Anybody who hasn't had the class probably have no idea what I'm talking about, but is anybody a chemist or have any lab experience that could help me out (or some specific journal articles will work as well)? I've put in enough effort that I'm going to get a good grade anyhow, but just for pride I actually want to get this shit to work.