Skip to main content
Get your brand new Wikispaces Classroom now
and do "back to school" in style.
Pages and Files
UC on ChemSpider
Alicia's Masters Thesis
Open Web Drug Dev.
To Do List
Ugi NMR Analysis
To synthesize a Ugi adduct from benzylamine, phenanthrene-9-carboxaldehyde, 4-chlorophenyl acetic acid and n-butyl isocyanide in methanol using Ugi 4CR following
. The target compound was ranked 18 in the
. The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this
To a one dram vial, charged with methanol (1mL) and benzylamine, phenanthrene-9-carboxaldehyde, 4-chlorophenyl acetic acid and n-butyl isocyanide (0.5mmol each) was added in that order. After each addition, the resulting solution was vortexed for at least 15 seconds and confirmed that a homogeneous solution had been obtained. The vial was capped tight and left at room temperature for 1 day.
ID/ Lib Rank
4-chlorophenyl acetic acid
0.5 mmol, 103.12 mg
0.5mmol, 85.30 mg
0.5mmol, 52.28 ul
Density information found on the Sigma-Aldrich website (www.sigmaaldrich.com)
5 min after mixing
all components (159A)
One day after mixing
all components (159B)
All results are recorded
Master Table and Workflow Tables
[So it looks like you get a clear solution when the phenanthrene-9-carboxaldehyde is mixed with benzylamine in methanol JCB]
After one day a precipitate was obtained but the solvent was evaporated without washing - aborted and to be repeated.
16:03- Started to weigh out the phenanthrene-9-carboxaldehyde.
16:09- Started to weigh out the 4-chlorophenyl acetic acid.
16:14- Charged a vial with 1 mL of methanol.
16:16- Added the benzylamine to the vial and vortexed for 15 seconds. A clear solution was obtained.
16:20- Added the phenanthrene-9-carboxaldehyde to the vial and vortexed for 5 minutes until a clear solution was obtained.
16:26- Added the 4-chlorophenyl acetic acid to the vial and vortexed for 15 seconds. A clear solution was obtained.
16:30- Added the n-butyl isocyanide to the vial and vortexed for 15 seconds. A clear solution was obtained.
16:33- Took a photo of the vial and left it to sit for 24 hours at room temperature.
16:38- Took a photo of the vial after one day. A most of the liquid in the vial precipitated into a solid.
15:34- Vortexed the product in the vial for 15 seconds. No solvent was visible.
15:36- Added 500 ul of methanol to the vial and vortexed for 15 seconds. The solvent remained over the solid.
15:40- Sonicated the vial containing undissolved solid and methanol on top for 1 min, then vortexed it for 15 sec. At this time the solid packing at the bottom of the vial mixed well with the solvent and a pasty mixture covered the walls of the vial.
15:43- The vial was then emptied onto a clean watch glass.
15:45- The vial was rinsed with 250 ul of methanol, and then the contents were emptied onto a watch glass.
15:47- A photo was taken (159C) of the watch glass and empty vial. The methanol will evaporate so the product can be weighed.
4-chlorophenyl acetic acid
help on how to format text
Turn off "Getting Started"