Objectives

  • To study the effect of concentration on the precipitation of ugi product
  • To synthesize three Ugi adducts from in methanol using Ugi 4CR following Explan005. If solid products are obtained, the experiment will serve as a template for an automated run. This experiment is a follow-up of Exp185 and Exp 187 varying the concentrations of the reagents used.

Procedure

To two one dram vials, charged with methanol (1mL), 4- (trifluoromethyl benzaldehyde (0.25mmol), respective amines (0.25mmol), methactrylic acid (0.25mmol) and t-butyl isocyanide (0.25mmol) was added in that order. After each addition, the resulting solution was vortexed for 15 seconds and confirmed that a homogeneous solution had been obtained. The vial was capped tight and left at room temperature..
Sample ID
Aldehyde
Amine
Acid
Isocyanide
Ppt (Y/N) & Yield
188-1
4- (trifluoromethyl) benzaldehyde
(0.25mmol-34.1uL)
5-Methylfurfurylamine
(0.25mmol-27.8L)
Methacrylic acid
(0.25mmol-21.2uL)
t-butylisocyanide
(0.25mmol-28.2uL)
N
188-2
4- (trifluoromethyl) benzaldehyde
(0.25mmol-34.1uL)
Benzylamine
(0.25mmol-27.3uL)
Methacrylic acid
(0.25mmol-21.2uL)
t-butylisocyanide
(0.25mmol-28.2uL)
N
188-3
4- (trifluoromethyl) benzaldehyde
(0.25mmol-34.1uL)
t-butylamine
(0.25mmol- 26.2uL)
Methacrylic acid
(0.25mmol-21.2uL)
t-butylisocyanide
(0.25mmol-28.2uL)
N

Results

Exp ID
Day1
Day-4
Final
188-1
188-1day1.JPG
188-1day4.JPG
No Ppt
188-2
188-2day1.JPG
188-2day4.JPG
No Ppt
188-3
188-3day1.JPG
188-3day4.JPG
No Ppt

Discussion

After 8 days of monitoring..no precipitate is observed. However sample 188-2 formed solid precipitate after 5 days when a higher concentration of reagents was used Exp187.

Conclusion

The conditions and reagent concentrations used is unsuitable to precipitate a ugi product for the given samples.

Log

2008-05-08

19:00 Added methanol (1mL) to three small vials labelled 188-1, 188-2 and 188-3. Then added 4- (trifluoromethyl) benzaldehyde to each vial, vortexed for 15s each. This was followed by the addition of respective amines (from the table above) to each vial, vortexed for 15s..then added methacrylic acid to each, vortexed 15s each and finally t-butyl isocyanide was added to the vials..vortexed for 15s.
20:30 Obtained pictures of the vials. (series - Day 1)

2008-05-09

10:00 Obtained pictures of the vials. (series - Day 4)

Tags

Chemical
Inchi
Inchikey
4- (trifluoromethyl benzaldehyde
InChI=1/C8H5F3O/c9-8(10,11)7-3-1-6(5-12)2-4-7/h1-5H
BEOBZEOPTQQELP-UHFFFAOYAG
5-Methylfurfurylamine
InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3
YSEAGSCGERFGBL-UHFFFAOYAH
Benzylamine
InChI=1/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2
WGQKYBSKWIADBV-UHFFFAOYAL
tert-butylamine
InChI=1/C4H11N/c1-4(2,3)5/h5H2,1-3H3
YBRBMKDOPFTVDT-UHFFFAOYAT
Methacrylic acid
InChI=1/C4H6O2/c1-3(2)4(5)6/h1H2,2H3,(H,5,6)
CERQOIWHTDAKMF-UHFFFAOYAE
t-butyl isocyanide
InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3
FAGLEPBREOXSAC-UHFFFAOYAL
188-2
InChI=1/C24H27F3N2O2/c1-16(2)22(31)29(15-17-9-7-6-8-10-17)20(21(3 ​0)28-23(3,4)5)18-11-13-19(14-12-18)24(25,26)27/h6-14,20H,1,15H2,2​ -5H3,(H,28,30)
KPGSTEQWODPHDS-UHFFFAOYAL
188-1
InChI=1/C23H27F3N2O3/c1-14(2)21(30)28(13-18-12-7-15(3)31-18)19(20 ​(29)27-22(4,5)6)16-8-10-17(11-9-16)23(24,25)26/h7-12,19H,1,13H2,2​ -6H3,(H,27,29)
SAWKKHAHHFXDJA-UHFFFAOYAY
188-3
InChI=1/C21H29F3N2O2/c1-13(2)18(28)26(20(6,7)8)16(17(27)25-19(3,4)5)14-9-11-15(12-10-14)21(22,23)24/h9-12,16H,1H2,2-8H3,(H,25,27)/i1-12,2-12,3-12,4-12,5-12,6-12,7-12,8-12,9-12,10-12,11-12,12-12,13-12,14-12,15-12,16-12,17-12,18-12,19-12,20-12,21-12,22-19,23-19,24-19,25-14,26-14,27-16,28-16