Objective

To synthesize a Ugi adduct from Phenanthrene-9-carboxaldehyde, 1-Hexylamine, Tert-butylisocyanide and Benzoic acid in methanol using Ugi 4CR following Explan005. This is a repeat of Exp143a.The target compound was ranked 64 in the DEXP014-V1B file from D-EXP014.

Procedure

To a one dram vial, charged with methanol (200uL) hexylamine, phenanthrene-9-carboxaldehyde, benzoic acid and tert-butyl isonitrile (0.5mmol each) was added in that order. After each addition, the resulting solution was vortexed for 15 seconds (or more) and confirmed that a homogeneous solution had been obtained. The vial was capped tight and left at room temperature for 1days. The obtained solid was washed with methanol (3 x 500uL), centrifuged each time to obtain a white residue. The wet product was set under a high vac to remove the solvent.
Characterization of 149
ID/ Lib Rank
Solvent
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
148A/153
Methanol
Phenanthrene-9-
carboxaldehyde
n-Hexylamine
Benzoic acid
tert-butylisocyanide

Quantity
1000uL
0.5mmol, 103.1mg
0.5mmol, 66.05uL
101.19g/mol
density- 0.766 g/mL at 25 °C(lit.)
(Sigma Aldrich)
0.5mmol, 61.06mg
122.12 g/mol
0.5mmol, 56.5uL
(density=0.735g/ml)
Yield -

Results

Phenanthrene-9-Carboxaldehyde (solid from Sigma-Aldrich)
HNMR
n-Hexylamine
HNMR
Bernzoic Acid
HNMR
tert-Butyl isocyanide
HNMR

the log does not report an image taken after one hour, only 4 hours after the addition of the last component - which is correct?
an hour after mixing
all components


Exp149A.JPG

Discussion



All results are recorded in the Master Table of all Ugi synthesis attempts

Conclusion

Unless a pic is provided to show presence or absence of precipitate, this experiment was aborted

Log

follow experimental forma (e.g. use military time) http://usefulchem.wikispaces.com/format

2007-11-27

4:30 200 ul was added to a one dram vial and the solution was vortex for 10s.
hexylamine was added to the vial and vortex for about 15s. no ppte was observed.
phenanthrene-9-carboxaldehyde was then added and stirred.
benzoic acid was then wieghed out and added to the vial and vortexed for 15s.
5:00 then butylisocyanide was then added to the vial under the hood and the solution was vortexed (how long?) and lleft in the hood.
8:50 photo taken after all reagents have been added and vortex.experiment will be redone the next day.
solution was then left in the hood overnight.
don't wait too long to take the next pic