Reactants


Solvent


Predicted Products

UC226-1 Predicted Ugi Product:
[All of the phenanthrene components are drawn incorrectly JCB] Thank you, they should be corrected now.
UC226-1new.png
UC226-2 Predicted Ugi Product:

UC226-2new.png
UC226-3 Predicted Ugi Product:

UC226-3new.png
UC226-4 Predicted Ugi Product:

UC226-4new.png
UC226-5 Predicted Ugi Product:
UC226-5new.png

UC226-6 Predicted Ugi Product:
UC226-6new.png

UC226-7 Predicted Ugi Product:
UC226-7new.png

UC226-8 Predicted Ugi Product:
UC226-8new.png

Objective

To synthesis eight different Ugi products.

Procedure

Label
Amount of Solution of Benzaldehyde, 5-Methyl furfurylamine, and 1-Pyrene butanoic acidwith THF (uL)
Isocyanide
Amount of isocyanide to be added (uL; mg for 226-6 and 226-8)
226-1
900
t-butylisocyanide
56.5
226-2
900
n-butylisocyanide
52.3
226-3
900
1-pentylisocyanide
63.0
226-4
900
cyclohexylisocyanide
62.2
226-5
900
benzylisocyanide
61.0
226-6
900
toluene-4-sulfonylmethylisocyanide (TOSMIC)
97.6
226-7
900
morpholinoethylisocyanide
69.0
226-8
900
2-chloro-6-methylphenylisocyanide
75.8

Results

Pictures

Note: Pictures have been compressed. High resolution photos are available.
UC226_01
UC226_02
UC226_03
UC226_04
UC226_05
UC226_06
UC226_07
UC226_08
UC226_09
UC226_10
UC226_11
UC226_12
UC226_13

Spreadsheet

UCExp226[Always put units in the column headings JCB]

Vial
Precipitate
226-1
No
226-2
No
226-3
No
226-4
No
226-5
No
226-6
No
226-7
No
226-8
No

Discussion

None of the Ugi products precipitated out of solution within 4 days.
[Add results to CombiUgi master table JCB]

Conclusion

Ugi products did not precipitate. Therefore, they are not useful for anti-malarial drug synthesis.

Log

2009-05-20
19:38 Weighed 5-mL volumetric flask (19.975 3 g)
19:46 Added 508 uL of benzaldehyde and weighed (20.549 2 g)
19:48 Added 557 uL of 5-methylfurfurylamine and weighed (21.128 2 g)
19:49 Vortexed for 20 sec
19:50 Added THF and weighed (21.765 6 g)
19:51 Vortexed for 10 sec
19:53 Added 0.144 2 g of 1-pyrenebutanoic acid and weighed flask (21.904 8 g)
20:01 Added THF up to 5-mL mark and weighed (24.608 7 g)
20:05 Vortexed for 10 sec
20:14 Parafilmed
20:14 Photo (UC226_01) - completely dissolved
20:14 Labeled (UCEXP226A)

2009-05-21
9:44 Photo (UC226_02) - no product (Note: Needed to added 1.441 7 g of 1-pyrenebutanoic acid instead of 0.144 2 g)
9:45 Cleaned and dried 5-mL volumetric flask
9:53 Weighed 5-mL volumetric flask (19.975 8 g)
9:58 Added 508 uL of benzaldehyde and weighed (20.541 8 g)
10:00 Added 557 uL of 5-methylfurfurylamine and weighed (21.126 0 g) - mixture was warm
10:02 Vortexed for 10 sec
10:02 Vortexed for 10 sec
10:03 Added THF with Pasteur pipet and weighed (21.422 9 g)
10:06 Added 1.441 7 g 1-pyrenebutanoic acid
10:33 Added THF up to 5-mL mark
10:38 Photo (UC226_03)
10:39 Parafilmed
10:40 Vortexed for 30 sec
10:41 Parafilmed again
10:42 Vortexed for 30 sec
10:43 Vortexed for 30 sec
10:45 Parafilmed again because parafilm sometimes melts in sonicator
10:47 Photo (UC226_04)
10:52 Began sonication (25 degrees Celsius) with copper wire support
11:02 Removed from sonicator
11:06 Added THF up to 5-mL mark
11:08 Vortexed for 30 sec
11:09 Photo (UC226_05)
11:09 Temperature in sonicator is 30 degrees Celsius
11:10 Parafilmed
11:11 Sonicated with copper wire support
11:40 Removed from sonicator (40 degrees Celsius)
11:41 Photos (UC226_06, UC226_07) - not dissolved
11:46 Added 100 uL of THF
11:47 Vortexed 30 sec
11:48 Added 100 uL of THF
11:49 Vortexed 30 sec
11:50 Added 100 uL of THF
11:51 Vortexed 30 sec
11:53 Added 100 uL of THF
11:56 Vortexed 30 sec
11:59 Transferred to large vial and rinsed with four 300 uL portions (1 200 uL) of THF
12:06 Vortexed for 30 sec
12:07 Vortexed for 30 sec
12:08 Photo (UC226_08)
12:10 Added 200 uL of THF
12:11 Vortexed for 30 sec
12:12 Added 200 uL of THF
12:13 Vortexed for 30 sec
12:14 Added 200 uL of THF
12:14 Vortexed for 30 sec
12:15 Added 200 uL of THF
12:16 Vortexed for 30 sec
12:17 Added 200 uL of THF
12:17 Vortexed for 30 sec
12:18 Added 200 uL of THF
12:19 Vortexed for 30 sec
12:21 Added 200 uL of THF
12:22 Vortexed for 30 sec
12:22 Added 200 uL of THF
12:23 Vortexed for 30 sec
12:24 Added 200 uL of THF
12:24 Vortexed for 30 sec
12:25 Added 200 uL of THF
12:26 Vortexed for 30 sec
12:27 Added 200 uL of THF
12:28 Vortexed for 30 sec
12:29 Added 200 uL of THF
12:30 Vortexed for 30 sec
12:31 Photo (UC226_09) - somewhat dissolved
12:39 Began sonication (24 degrees Celsius)
13:04 Finished sonicating (41 degrees Celsius)
13:08 Photo (UC226_10) - completely dissolved
15:10 Attempted to add 900 uL of the solution of benzaldehyde, 4-methylfurfurylamine, 1-pyrenebutanoic acid, and THF to eight 1/2 dram vials, but the mechanical pipet would not hold the liquid
15:13 Labeled vials (226-1 through 226-8)
15:17 Weighed vials
Label
Mass (g)
226-1
2.392 8
226-2
2.418 0
226-3
2.415 5
226-4
2.412 0
226-5
2.394 4
226-6
2.424 7
226-7
2.409 3
226-8
2.413 8
16:03 Transfered solution of benzaldehyde, 4-methylfurfurylamine, 1-pyrenebutanoic acid, and THF to large vial
16:05 Photo of large vial (UC226_11)
16:06 Added 900 uL of solution in large vial to eight 1/2 dram vials using different mechanical pipet
16:11 Photo (UC226_12)
16:12 Weighed vials
Labels
Mass (g)
226-1
3.216 0
226-2
3.235 8
226-3
3.312 6
226-4
3.231 3
226-5
3.219 5
226-6
3.349 9
226-7
3.323 6
226-8
3.345 2
16:20 Added isocyanides
Isocyanide
Amount (uL for liquids; mg for solids)
t-butylisocyanide
56.5
n-butylisocyanide
52.3
n-pentylisocyanide
63.0
cyclohexylisocyanide
62.2
benzylisocyanide
61.0 (Not enough - redo: 226-5REDO)
Toluene-4-sulfonylmethylisocyanide (TOSMIC)
97.6
Morpholinoethylisocyanide
69.0
2-chloro-6-methylphenylisocyanide
75.8
17.38 Weighed vials
Label
Mass (g)
226-1
3.254 5
226-2
3.274 6
226-3
3.360 6
226-4
3.283 8
226-5
3.274 9
226-5REDO
3.340 6
226-6
3.431 5
226-7
3.403 2
226-8
3.407 0
17:47 Vortexed for 30 sec
17:54 Began sonication (23 degrees Celsius)
18:24 Remove from sonicator (35 degrees Celsius). Note: Labels 226-1, 226-2, 226-3, 226-4, 226-5, and 226-6 washed off by sonication; only labels 226-5REDO, 226-7, and 226-8 remain. Therefore, NMR will be also be used to determine sample identity.
18:40 Photo (UC226_13)
18:44 Placed vials in 100-mL beaker and parafilmed beaker

2009-05-26
11:15 Still no precipitate in any of the vials.