Researchers

Hai Truong and Khalid Mirza

Objective

To study the effect of imminium (of phenanthrene-9-carboxaldehyde+ furfurylamine+phenylacetic acid) on the solubility of the Ugi product UCExp176C in methanol
Co-solutes
a) phenanthrene-9-carboxaldehyde+ furfurylamine+phenylacetic acid (0.1M, 0.06M, 0.02M) in both benzene and methanol


Procedure

153A- 0.1M : Weigh out fufurylamine (0.21mmol, 20mg) in a 2mL volumetric flask. Add a small volume of methanol to it. Then weigh out phenanthrene-9-carboxaldheyde (0.2mmol, 43mg) and add it to the amine/methanol solution, This is imine/methanol solution. Then weigh out phenylacetic acid (0.2mmol, 28mg)and add it to the imine/methanol solution. Make it up to the mark with methanol. Use this as a stock solution- 153A.-0.1M
153-B - 0.06M Pipette out 600uL of 153A in to a 1mL volumetric flask and make it up to the mark with methanol
153-C - 0.02M Pipette out 200uL of 153A in to a 1mL volumetric flask and make it up to the mark with methanol

SpreadsheetONSCExp153-i

Log

12-04-2009
15:45 Took out a 2ml volumetric flask to make up 153A-0.1M solution. Weighted out 20mg of fufurylamine in 2ml volumetric flask. Then added a small amount of methanol to it.
15:50 Weighed out 43mg of phenanthrene-9-carboxaldehyde, and put it into the flask above. Then add a little methanol to it. This is amine/methanol solution.
16:00 Weighed out 28mg of phenylacetic acid, and added it to the flask. Put more methanol to make it to the mark. This was used as stock solution 153A-0.1M
16:10 Took out two 1ml volumetric flasks. Labeled B and C.
To flask B: pipetted out 600uL of 153A and put into flask B. Filled up to the mark with methanol.
To flask C: pipetted out 200uL of 153A and put into flask C. Filled up to the mark with methanol.
16:30 Took out three half dram vials. Labeled Exp153-A, Exp153-B and Exp153-C:
To vial Exp153-A: pipetted out 500uL from stock solution 153A. Put small amount of Ugi 176C into it so that there was still small amount of solid remained in the solution.
To vial Exp153-B: pipetted out 500uL from flask B. Put small amount of Ugi 176C into it so that there was still small amount of solid remained in the solution.
To vial Exp153-C: pipetted out 500uL from flask C. Put small amount of Ugi 176C into it so that there was still small amount of solid remained in the solution.
16:40 Parafilmed all the vials
16:45 Put all vials into Lauda heating/cooling bath. The temperature in the bath was 40C
12-05-2009
11:10 Changed the temperature setting of the water-glycol to 25C.
16:10 Removed the vials from the temperature control bath and centrifuged them...S
16:20 Obtained six one dram vials and transferred out approximately 400uL DMSO0d6 in to them and labeled A, B and C
17:00 After centrifuging the half dram vials B through H, carefully transferred out approximately 200uL supernatant from each into corresponding '2' series vials. The resulting solutions in one dram vials with DMSO-d6 are labeled ONSCExp153A, ONSCExp153B and ONSCExp152C
21:35 Completed obtaining HNMRs of the samples.