I'm trying to figure out the following reaction mechanism
There's a reference paper by Yanagi and Akiyoshi(1959) showing the hydroxyethylation of imides resulting in the following
I have two questions :
(1) Why would the hydroxylethylation occur in the 1 position instead of the imide at the 3 position? I would imagine that this reaction occurs for the more acidic amine, but I have no idea why there doesn't seem to be any literature about that reaction.
(2) Why would this reaction produce a HydroxyEthyl and not a urethane, as shown here :
Any insights would be appreciated, thanks!
Yanagi and Akiyoshi : http://pubs.acs.org/doi/abs/10.1021/jo01090a601
Reaction in red (from a patent application): http://www.huntsman.com/performance_products/Media%20Library/a_MC348531CFA3EA9A2E040EBCD2B6B7B06/Products_MC348531D0B9FA9A2E040EBCD2B6B7B06/Carbonates_MC348531D1109A9A2E040EBCD2B6B7B06/files/jeffsol_alkylene_carbonates_synthesis_of_hydroxy_alkyl_urethanes.pdf