[clyde]

I would like to convert ethyl lactate to amide (more precisely amino amide, I want to use ethlyenediamine as a precursor). Anyone knows reaction conditions? I tried refluxing in acetone, but seems no progress. Maybe DMSO, over 100 degrees with some acid catalyst? Thx

[sjb]

What else do you have in the molecule?

I've had some success forming the aluminium amide from amines with AlMe₃ (careful, rather pyrophoric), at around 0 deg C in dry toluene, then adding a methyl ester to form the amides and allowing to slowly warm to rt.

My molecule had a 2-chloropyrimidine in it as well, that was untouched (no evidence rom LC-MS / ¹H NMR etc), so I guess it's reasonably robust, maybe it was just favoured at the lower temperature compared to the chlorine displacement.

[sjh9]

I would like to convert ethyl lactate to amide (more precisely amino amide, I want to use ethlyenediamine as a precursor). Anyone knows reaction conditions? I tried refluxing in acetone, but seems no progress. Maybe DMSO, over 100 degrees with some acid catalyst? Thx

Are you trying to react 2 eq of ethyl lactate with the amines on EDA?  Either way both are liquid and I believe miscible.  Mix them in the desired ratios (one amide = major excess EL, 2 amides =major excess  EDA) and reflux.  You could use a solvent but not a ketone especially with a bp under 100.
This probably would work in an bomb reactor as well.  Rotovap off the excess EDA or LA.  Either way this will not be the cleanest reaction.  LA can polymerize but more likely you'll get a lot of dilactate as a side product.

[clyde]

I want to have free amino end so I added 5 molar excess of EDA. In acetone some strange side reaction occurs. I will change the solvent today, DMSO preferably. If you have some other compound which will result in the free amino end an my lactate (or lact. acid) please say.

[sjh9]

I want to have free amino end so I added 5 molar excess of EDA. In acetone some strange side reaction occurs. I will change the solvent today, DMSO preferably. If you have some other compound which will result in the free amino end an my lactate (or lact. acid) please say.

I think in your case you could use EDA as the solvent and remove the excess under vacuum.  It would be easier to remove than DMSO.  If you require an additional solvent for some reason I suggest DMF before DMSO.

Just out of curiosity, how are you monitoring this reaction?

[clyde]

By TLC, MeOH as a mobile phase

[lutesium]

If we look at the synthesis of barbituric acid from diethyl malonate and urea we use a solvent EtOH + NaEthoxide!!!

Maybe this might also work in your process!!!


Lutesium...