Exp224

=Objective= To synthesize eight Ugi products with benzaldehyde, propylamine and 1-pyrenebutyric acid with eight different isocyanides in THF. =Procedure= A homogeneous solution of benzaldehyde (5mmol, 508uL), propylamine (5mmol, 411uL) and 1-pyrenebutyric acid (5mmol, 1441.7mg) was made up in 5mL volumetric flask. The solution (500uL, 0.5mmol per component) was transferred in to eight labeld one dram vials. To each vial a unique isocyanide (0.5mmol) was added. The obtained solutions were vortexed for 10s each to ensure a homogeneous solution was obtained. The vials containing the reaction mixtures were left undisturbed overnight at room temperature. = = =Results= Pictures [|IMG-UCExp224-1] [|IMG-UCExp224-2] [|IMG-UCExp224-3] [|IMG-UCExp224-4] [|Spreadsheet] media type="custom" key="3843805" =Discussion= None of the solutions formed any crystalline product; therefore it is assumed that it is not very likely to prepare crystalline Ugi products of 1-pyrenebutyric acid in THF with benzaldehyde, propylamine and the isocyanides used at about 0.9M concentration per component.

=Conclusion= No Ugi products precipitated out from THF solution of the starting materials used at a concentration of about 0.9M per component.

=Log= 17:00 A one molar solution of benzaldhyde, propylamine and 1-pyrenebutyric acid was made-up in a 5mL volumetric flask by placing benzaldehyde (5mmol, 508uL), THF (~2mL initially), propylamine (5mmol, 411uL) and 1-pyrenebutyric acid (5mmol, 1441.7mg). The solution was made-up to the mark by adding required amount of THF....most of the acid dissolved in the solution immediately, however some of it still remained undissolved at the bottom, therefore sonication was applied. 17:30 Placed the volumetric flask in the sonciation with water bath at room temp (20C), obtained a picture (IMG-UCExp224-1) of the volumetric flask in the sonicator. 17:45 Removed the flask from the sonicator (no change in the temp in the water bath); all the acid appeared to have dissolved in the solution. 17:55 Obtained a picture (IMG-UCExp224-2) of the clear solution in the volumetric flask..this solution is labeled **'224-O'** 18:20 Labeled eight vials as **224-1, 224-2, 224-3, 224-4, 224-5, 224-6, 224-7** and **224-8**. 18:25 Placed 500uL of the solution 224-O in to the above labeled eight vials 18:50 Added the following isocyanides to the corresponding vials. After the addition of the isocyanide to the vials they were vortexed for 10s and made sure a homogeneous solution was obtained. isocyanide added(0.5mmol) || 19:20 Obtained a picture (IMG-UCExp224-3) of the vials containing eight solutions ..Not sure why but appears like most solution vials have accumulated some amount of solid at the bottom of the vials...wonder if the reaction rate is so fast that the Ugi products crystals are falling out of the solution or if 1-pyrenebutyric acid is...infact it would be weird if the acid is falling out, because a homogenenous solution of 224-O was definitely obtained after sonication.. 22:00 Obtained a picture of the solutions in the vials; hardly any changes noticeable in any of the vials (IMG-UCExp224-4)...vial 224-6 which had TOSMIC shows some ppt..believe it could be the isocyanide that might have crashed out. In almost all the vials there is some coating of a powdery mass at the bottom of the vials, which may be one of the starting materials crashing out.
 * 2009-05-19**
 * Sample Number || Isocyanide added || Amt of
 * 224-1 || t-butylisocyanide || 56.5uL ||
 * 224-2 || n-butylisocyanide || 52.3uL ||
 * 224-3 || n-pentylisocyanide || 63uL ||
 * 224-4 || cyclohexylisocyanide || 62.2uL ||
 * 224-5 || benzylisocyanide || 61uL ||
 * 224-6 || TOSMIC || 97.6mg ||
 * 224-7 || Morpholinoethyl isocyanide || 69uL ||
 * 224-8 || 2-chloro-6-methylphenyl isocyanide || 75.8mg ||
 * 2009-05-20**