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UC on ChemSpider
Alicia's Masters Thesis
Open Web Drug Dev.
To Do List
Ugi NMR Analysis
To check the stability of the furan ring of 5-Methylfurfurylamine (5-MFA) in TFA to investigate
the behavior of furan containing Ugi products
. According to the
, a similar elimination of ammonia is expected for 5-MFA
A solution of 5-methyl furfurylamine (223uL, 2mmol) and pure TFA (3mL) in a 10ml round bottom flask, with a condenser was heated for about 30 min under N2.
until start of reflux is determined we don't know the reflux time
It is possible to determine the amount of starting material remaining after T1 and T2 by looking at the ratio of furan H's to the TFA peak. Also discuss the new peaks that show up.
The furan ring is shown to be unstable when dissolved in pure TFA and refluxed for about 24 hours, however it survived for the first half an hour at least.
14:40 Added TFA (3mL) to 5-methyl furfurylamine (223uL, 2mmol) in 10ml single necked round bottom flask with a reflux condenser, this is
Video of setup
14:41 Measured 100uL of solution
and dissolved it in CDCl3 (800uL)
14:47 Started heating and stirring solution in flask (variac setting 80),
14:53 The solution started to reflux
15:13 Stopped heating (solution was boil over into the condenser), took out of sand bed to cool, this solution became
15:16 Measured 100uL of solution from flask and dissolved it in CDCl3 (800uL)
15:37 Obtained HNMR of 112A
15:39 Obtained HNMR of 112B-T1 (after heating)
15:41 Put solution in flask back on heat with variac setting at 80.
15:47: The solution started to reflux.
15:55 Turned heat down to 40.
16:25 Took flask with solution off of heat, this is
16:37 Measured 100uL of solution
and dissolved in CDCl3 (800uL)
16:44 Obtained HNMR of 112B-T2 (after second heating)
17:00 Starting heat again under same conditions (variac setting at 40), stirring
11:45 Removed the flask from heat source. The solution was refluxed overnight.
12:31 After the solution had cooled a few drops of it was taken up in CDCl3 (800uL) in an NMR tube and an H NMR was obtained, this is recorded as
.The solution remained almost insoluble in CDCl3.
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