Researcher

David Bulger

Objective

Determine the solubility of Ugi Product 148B from UC148 , which also corresponds to 148B in the Isolated Compounds Sheet, in six solvents (methanol, ethanol, THF, acetonitrile, DMSO, toluene).

Procedure

Make saturated solutions of Ugi Product 148B in the methanol, ethanol, THF, acetonitrile, DMSO, and toluene. Determine solubility using SAMS and internal standard (IS) methods.

Results

NMR

ONSC096DN[what is the difference bewteen DN,DM and DR? JCB] The solution from D3 was transferred into three different vials, which was transferred to three different NMR tubes with three different pipets. They are different in the transfer from vial D3 to NMR tube.
ONSC096DM
ONSC096DR
ONSC096FN
ONSC096FM
ONSC096FR

Raw JCAMP-DX File for ONSC096DN
Raw JCAMP-DX File for ONSC096DM
Raw JCAMP-DX File for ONSC096DR
Raw JCAMP-DX File for ONSC096FN
Raw JCAMP-DX File for ONSC096FM
Raw JCAMP-DX File for ONSC096FR

Pictures

ONSC096-1
ONSC096-2ONSC096-3ONSC096-4

Spreadsheets

ONSC096-1
ONSC096-2

Solubilities

Vial
Solvent
SAMS Solubility (M)
IS Solubility (M)
ONSC096A
Methanol


ONSC096B
Ethanol


ONSC096C
THF


ONSC096D
Acetonitrile
0.02, 0.02, 0.02
0.03, 0.04, 0.04
ONSC096E
DMSO


ONSC096F
Toluene
0.14, 0.14, 0.14
0.14, 0.16, 0.15
Note: Need to make more Ugi Product to finish solubility measurements.

Discussion

There was only enough Ugi Product to make saturated solutions in acetonitrile and toluene, which yielded solubilities of 0.02 M and 0.14 M respectively using SAMS and 0.03 M and 0.14 M respectively using IS.

Conclusion

Solubility of Ugi Product 148B in acetonitrile was found to be 0.02 M and in toluene was found to be 0.14 M using SAMS and 0.03 M and 0.14 M respectively using IS.

Log

2009-05-22
11:05 Labeled eight 1/2 dram vials (ONSC096A through ONSC096F)
11:08 Weighed vials
Vial
Mass (g)
ONSC096A
2.416 6
ONSC096B
2.434 3
ONSC096C
2.427 3
ONSC096D
2.405 8
ONSC096E
2.399 0
ONSC096F
2.416 2
11:15 Added 900 uL of each solvent to respective vials and weighed
Vial
Solvent
Mass (g)
ONSC096A
Methanol
3.159 1
ONSC096B
Ethanol
3.165 0
ONSC096C
THF
3.220 6
ONSC096D
Acetonitrile
3.135 0
ONSC096E
DMSO
3.398 0
ONSC096F
Toluene
3.219 0
13:34 Added Ugi Product 216-7A to vials and weighed
Vial
Mass (g)
ONSC096A
3.175 7
ONSC096B
3.196 0
ONSC096C
3.246 2
ONSC096D
3.160 1
ONSC096E
3.443 9
ONSC096F
3.262 7
13:45 Vortexed for 30 sec
13:47 Photo (ONSC096-1)
13:49 Added Ugi Product to ONSC096A and ONSC096C
Vial
Mass before addition (g)
Mass following addition (g)
ONSC096A
3.175 7
3.181 2
ONSC096C
3.246 1
3.247 3 (Not enough Ugi product to saturate)
13:56 Added Ugi Product to ONSC096A (3.247 3 g)
13:58 Vortexed ONSC096A and ONSC096C for 30 sec
13:59 Photo of ONSC096A and ONSC096C (ONSC096-2)
14:05 Began sonication (27 degrees Celsius)
14:35 Removed from sonicator (35 degrees Celsius)
14:38 Photo (ONSC096-3)
17:13 Centrifuged for 3 min
17:19 Photo (ONSC096-4) - only ONSC096D and ONSC096F are saturated
17:21 Transferred ONSC096D to D1 and ONSC096F to F1 (1/2 dram vial)
17:23 Centrifuged D1 and F1 for 3 min
17:25 Transferred D1 to D2 and F1 to F2
17:29 Centrifuged D2 and F2 for 3 min
17:30 Weighed D3 (2.446 2 g) and F3 (2.402 8 g)
17:33 Transferred D2 to D3 and F2 to F3 (1/2 dram vial)
17:36 Weighed D3 (2.729 4 g) and F3 (2.925 0 g)
17:40 Weighed vials:
Vial
Mass (g)
DN
2.399 0
DM
2.401 0
DR
2.437 3
FN
2.387 4
FM
2.407 9
FR
2.421 7
17:50 Added 100 uL of D3 to DN, DM, and DR
17:51 Added 100 uL of F3 to FN, FM, and FR
17:52 Weighed vials:
Vial
Mass (g)
DN
2.472 2
DM
2.475 6
DR
2.514 4
FN
2.472 5
FM
2.495 4
FR
2.509 0
17:56 Added 700 uL chloroform-d and weighed:
Vial
Mass (g)
DN
2.545 8
DM
2.628 1
DR
2.662 1
FN
2.458 2
FM
2.653 0
FR
2.681 0
Vortexed for 10 sec
6:13 Added 10 uL of 1,2-dichloroethane and weighed:
Vial
Mass (g)
DN
2.555 9
DM
2.635 7
DR
2.672 4
FN
2.467 5
FM
2.663 7
FR
2.694 3
Vortexed for 10 sec
20:40 Transferred solutions to NMR tubes with corresponding labels (ONSC096DN, ONSC096DM, ONSC096DR, ONSC096FN, ONSC096FM, ONSC096FR)
21:00 NMR (ONSC096DN)
21:18 NMR (ONSC096DM)
21:25 NMR (ONSC096DR)
21:35 NMR (ONSC096FN)
21:46 NMR (ONSC096FM)
21:52 NMR (ONSC096FR)

References


Solubility of Ugi Product 148B in Organic Solvents
Solubility of Ugi Product 148B in Acetonitrile (solubility data viewer)
Solubility of Ugi Product 148B in Toluene (solubility data viewer)