Exp149

=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. carboxaldehyde || n-Hexylamine || Benzoic acid || tert-butylisocyanide ||  || 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** - ||
 * Characterization of 149**
 * ID/ Lib Rank || Solvent || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt Yes/No ||
 * 148A/153 || Methanol || Phenanthrene-9-
 * Quantity || 1000uL || 0.5mmol, 103.1mg || 0.5mmol, 66.05uL

=Results= [|HNMR] HNMR HNMR [|HNMR]
 * Phenanthrene-9-Carboxaldehyde** (solid from Sigma-Aldrich)
 * n-Hexylamine**
 * Bernzoic Acid**
 * //tert-B//utyl isocyanide**

all components** ||  || =Discussion=
 * //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
 * [[image:Exp149A.JPG width="138" link="http://usefulchem.wikispaces.com/space/showimage/Exp149A.JPG"]] ||  ||

All results are recorded in the [|Master Table of all Ugi synthesis attempts] =Conclusion= =Log=
 * //Unless a pic is provided to show presence or absence of precipitate, this experiment was aborted//**
 * //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//**