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 Benzophenone, Aniline,
in methanol using Ugi 4CR.
Dissolved benzophenone (182 mg, 1 mmol) and aniline(104.6 uL, 1.1 mmol, 10% excess ) in 2 mL methanol-d4 in a 4 mL volumetric flask, immediately transferred the contents to an NMR tube. The reaction was monitored by NMR. The reaction was left overnight to complete forming an imine. The next day a solution of
175 mg,1 mmol), and
(113 uL, 1 mmol) is made up in 4 ml volutmeric flask in methanol. This solution of is added to the preformed Imine. The reaction mix is allowed to sit undisturbed for 6-8, when the Ugi product is obtained. The product is recrystallized from a small amount of methanol analyzed by NMR and saved in a 1 dram vial.
(methanol-d4) spectrum does not appear decoupled - peaks showing up as doublets
t = 04 min
t = 07 min
t = 09 min
t = 34 min
t = 41 min
t = 45 min
= 55 min IR
t = 02 h 40 min
t = 02 h 45 min
t = 03 h 23 min
t = 03 h 44 min
t = 18 h 11 min
t = 18 h 32 min
(after 5days of addition of 92A to Boc-Gly and
There is no change in the H NMR even 18 h after mixing benzophenone with aniline and thus no evidence of imine formation.
Compare this with other reports of imine formation - see
page for reaction of aniline with ketones.
The experiment has reached a dead end.
Although before starting this reaction it was not known that aniline does not react with benzophenone under the conditions applied, however a reference[
] & [
] which indicates the unreactive behavior was found later.
Experiment aborted, (Imine did not form)
17:56 Made up a solution of solution of benzophenone and aniline in methanol-d4.
18:00 Obtained H NMR of 93A t = 04 min
18:03 Obtained H NMR of 93A t= 07 min
18:05 Obtained H NMR of 93A t= 09 min
18:30 Obtained C NMR of 93A t = 34 min
18:37 Obtained H NMR of 93A t = 41 min
18:41 Obtained H NMR of 93A t = 45 min
18:51 Obtained an IR of 93A t = 55 min
20:36 Obtained C NMR of 93A t = 02 h 40 min
20:41 Obtained HNMR of 93A t = 02 h 45 min
21:19 Obtained C NMR of 93A t = 03 h 23 min
21:40 Obtained H NMR of 93A t = 03 h 44 min
12:07 Obtained H NMR of 93A t = 18 h 11 min
12:28 Obtained C NMR of 93A t = 18 h 32 min
12:40 Made up a solution of Boc Glycine and tert-butylisocyanide in a 2 ml volutmeric flask in methanol (
12:43 Added the aminoacid / isonitrile solution to 93A. This multicomponent reaction mixture is now labelled
15:19 Obtained H NMR of 93B
1.Arndtsen, B., A.; Sleiman, H., F.; Chang, A., K.; McElwee-White, L.;J. Am. Chem. Soc.,
(13), pp 4871–4876
2 Ross, N., A.; MacGregor, R., R.; Bartsch, R., A.; Tetrahedron, 60 (9) 23, pp 2035-2041;
help on how to format text
Turn off "Getting Started"