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Solubility book (3rd Edn)
To estimate the co-solutes effect of phenanthrene-9-carboxaldehyde, furfurylamine and phenylacetic acid (equimolar) on the solubility of the Ugi product 176C(UC) in ethyl acetate
To a 0.37M solution (200uL) of phenanthrene-9-carboxaldehyde, furfurylamine and phenylacetic acid (per component) in ethyl acetate, the Ugi product 176C(UC) was added and ensured that further dissolution was not possible manually at room temp. This was done by vortexing the solution for approximately one minute.
The solution was then placed in a water/glycol bath at 40C for 1h. The temp of the bath was then reduced to 25C and the sample was left in it for another 1h. The solution was then centrifuged and the supernatant obtained was subjected to HNMR. Solubility was measured by the SAMS method.
[Include the measurements of the 3 components and specify the range you are using to try to measure the Ugi product. JCB]
No Ugi product was found in a 0.37M three component (co-solutes) solution.
[The SAMS spreadsheet is not filled in properly to make this statement JCB]
I do not see any Ugi product in the expected locations. Even if it is present, it is either is such negligible amounts that NMR may not be appropriate to measure its concentration accurately.
The Ugi product is insoluble in ethyl acetate with co-solutes.
13:00 Powered on the water/glycol temperature bath and set it to 40C.
13:30 A 0.37M three component solution of phenanthrene-9-carboxaldehyde, furfurylamine and phenylacetic acid ethyl acetate (200uL) was obtained from
(refer to the log there for its preparation) in a half dram vial labeled ONSCExp166-1A
13:35 Added Ugi product 176C (UC) in to the vial and made sure some of it remained undissolved even after vortexing it for one minute.
13:40 Parafilmed the vial and placed in the water/glycol bath at 40C.
15:50 Changed the temperature setting on the bath to 25C.
16:20 Temp recorded- 25C
17:30 Removed the vial from water/glycol temp bath, centrifuged it.
17:40 Carefully pipetted out the supernatant (100uL) in to a one dram containing ~800uL CDCl3. Capped the vial and vortexed it.
17:45 Pipetted out the solution in to an NMR tube and obtained an HNMR.
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