Hai Truong and Khalid Mirza


To measure the solubility of the Ugi product UC176C in methanol with a) ~0.05 imine b) imine + phenylacetic acid.


Make-up 0.05M imine by putting 0.025mmol (52mg) phenanthrene-9-carboxaldehyde + 0.025mmol (22ul) fufurylamine into 5ml volumetric flask and fill to the mark with methanol.
From 5ml 0.05M imine:
  1. Transfer to two half dram vials, each vials 1ml 0.05M imine.
  2. Transfer 2ml to a dram vials, put 0.1mmol(14mg) phenylacetic acid. Then, transfer ths 2ml into 2 half dram vials, each one 1ml.




Unlike benzene, there appears to be no affect of co-solute (imine and immminium phenylacetate) on the solubility of the Ugi product 176C in methanol. This could be an important reason as to why the product crashes out of methanol faster than from benzene in a Ugi reaction of phenanthrene-9-carboxaldehyde, furfurylamine, phenylacetic acid and n-butylisocyanide, UCExp251
The solubility of 176C in methanol had been previously measured between 0.02M and 0.08M.
Results from this experiment at 0.01M are close to its solubility in methanol measured in Exp065. Therefore there appears to be hardly any affect of co-solute on the solubility of UC176C in methanol.


A negligible affect of co-solutes (imine and immminium phenylacetate) was determined on the solubility of the Ugi product 176C in methanol. In both systems its solubility has been measured at 0.01M.


13:10 Weighed out 52mg phenanthrene-9-carboxaldehyde and put into a 5ml volumetric flask.
13:20 Put 22uL fufurylamine in the 5ml volumetric flask. Filled to the mark with methanol. This is a 5ml 0.05M imine solution.
13:40 Took out 2 half dram vials. Labeled ONSCExp151-1A, ONSCExp151-2A, ONSCExp151-3A, and ONSCExp151-4A.
13:45 Transfered to vials ONSCExp151-1A, ONSCExp151-2A, each 1ml of 0.05M imine solution.
14:00 Transfered 2ml of 0.05M imine solution to a 2ml volumetric flask up to the mark. Then weighed out 14mg phenylacetic acid, and put into the 2ml volumetric flask. As a result, this solution had total volume of 2.012ml. Then transfered this 2.012ml solution into 2 vials ONSCExp151-3A, ONSCExp151-4A with equal volume, so each of them ~1ml.
14:30 Put to 4 vials small amount of Ugi 176C. There was still solid remained in each vials. Vortexed them.
14:45 Farafilmed all vials.
15:00 Put all vials into Lauda heating/cooling bath. Adjust the temperature to 40C
15:20 Temperature in the bath was 40C
15:50 Temperature reached 25C
17:20 Removed the samples from the temperature bath at 25C and centrifuged the vials.
17:35 Labeled four one dram vials, ONSCExp151-1B, ONSCExp151-2B, ONSCExp151-3B and ONSCExp151-4B. Pipetted out DMSO-d6 (~ 300uL) in to each vial.
17:50 Pipetted out ~500uL supernatant from the previously centrifuged 'A' series vial in to corresponding 'B' series vials containing deuterated solvent. Vortexed the resulting solutions.
18:00 Transferred the 'B' series solutions in to four clean/dry NMR tubes.
19:00 Obtained HNMRs of ONSCExp151-1B, ONSCExp151-2B, ONSCExp151-3B and ONSCExp151-4B.