Objective

Ascertain the solubility of the Ugi adduct in Methanol, Ethanol, Acetonitrile, Tetrahydrofuran, Acetone, Hexane, Chloroform, and Distilled Water.

Procedure

Pipette ≈ 2mL of each solvent into four separate vials.
Gradually add Ugi adduct, using sterilized (alcohol rinsed) spatula, to each vial until solution no longer remains clear once shaken.
Once excess Ugi adduct sample settles towards the bottom of the vial, filter 1mL of clear saturated liquid for speed vac assay.

Material
Solvents:
THF - Tetrahydrofuran, stabilized anhydrous 99.9%
Lot# B0307053 AcroOrganics
Methanol
Ethanol - 200 Proof
Catalog# 111 AG S200 111 USP 200 111000200 Pharmco-AAper
Acetonitrile - HPLC - 99.9%
Lot# 75-05-8 AcroOrganics
Hexane
Lot# 061507A BDH
Choloform ≈ 99%
Batch# 00751LD Sigma Aldrich
Acetone
Water (distilled)
Solute:
Ugi Product first obtained in Exp099

Results

- the solubilities are all several orders of magnitude off - report in mM as indicated in the heading - some numbers are clearly impossible - the balance does not measure to the hundredth of a mg but 0.04 mg is reported - also indicate the mw used in the calculation - feel free to add more columns to clarify - add a column for time spent in speedvac
Solvent
Volume of the
Solution (mL)

Weight of the
empty vial (g)

Weight of the vial after
solvent evaporation (g)

Solubility of the
Ugi product (mg/mL)

Solubility (mM)
Time Spent in Speed-vac (hrs)
Acetonitrile (Trial #1)
1
2.21003
2.21419
4.16
9.38E-03
1
Acetonitrile (Trial #2)
1
2.05593
2.18171*
125.78*

1
THF (Trial #1)
0.5
2.21480
2.23364
37.68
8.50E-02
1
THF (Trial #2)
1
2.01536
2.04207*
26.71*

1
Ethanol (Trial #1)
0.5
2.21120
2.21334
4.28
9.65E-03
1
Ethanol (Trial#2)
1
2.00605
2.02832*
22.27*

1
Chloroform
1
2.20921
2.30914
99.93
2.25E-01
1
Methanol (Trial #1)
1
2.21177
2.22132
9.55
2.15E-02
1
Methanol (Trial #2)
1
2.04677
2.05529*
8.52*

1
Hexane
1
2.21784
2.21784
0
0
1
Acetone
1
2.20660
2.21497
8.37
1.89E-02
1
Water (distilled)
1
2.22357
2.22361
0.04
9.02E-05
1
*- Need further drying.
The obtained solubilities are recorded in the Solubilities spreadsheet

Discussion

Cloudy solutions indicate points surpassing level of saturation.
There is a significant variation in the solubilities from trial #1 and trial#2; this could be reflective of the fact that the trial#2 drying/evaporation time was only 30min compared to four hours for trial 1. Therefore the vials with the residues could still be wet and may need further drying. The times reported in the discussion do not match those reported in the table or the log!

Conclusion


Log


2008-08-18
11:39 - Ugi product recrystalized and rid of any impurities.what exactly was done? link to the source of this material and proof of purity by NMR
11:54 - Materials gathered (Methanol, Ethanol, THF, Acetonitrile)
12:30 - 2mL of methanol measured into vial and Ugi product added and mixed. AS
12:32 - 2mL of acetonitrile measured into vial and Ugi product added and mixed. CT
12:37 - 2mL of THF measured into vial and Ugi product added and mixed. Methanol cleared up. AS
12:39 - 2mL of ethanol measured into vial and Ugi product added and mixed. CT
12:41 - More Ugi added to methanol. As
12:43 - More Ugi added to THF. AS
12:52 - More Ugi added to THF. AS. All solutions appear saturated and cloudy.
6:00 - Solutions appear saturated with residue at the bottom of the vials. Each vial was vortexed for 10 seconds (vial containing chloroform was vortexed for 3 intervals of 20 seconds) to insure complete mixing.
6:44 - 2mL of Chloroform measured into vial and Ugi product added and vortexed. AS
6:45-6:52 - Ugi added to chloroform and vortexed 4 more times. Solution appears cloudy. AS
6:50 - 2mL of Acetone measured into vial and Ugi product added and vortexed. CT
6:51 - Ugi product added to Acetone and vortexed. Solution appears cloudy. CT
6:52 - 2mL of Hexane measured into vial and Ugi product added and vortexed. CT
6:53 - 2mL of DI water measured into vial and Ugi product added and vortexed. Solution does not appear to mix. AS
6:53 - Ugi product added to Hexane. Solution appears cloudy.
6:56 - All eight solutions left in closed vials overnight to vacuum centrifuge in the morning.
2008-08-19
11:40 - Acetonitrile filtered through buchner funnel. AS you can save time and reduce probability of contamination by filtering through a Pasteur pipette with a small cotton plug next time
11:42 - THF filtered through buchner funnel. AS
11:44 - Ethanol filtered through buchner funnel. AS
11:47 - Chloroform filtered through buchner funnel. AS
11:49 - Methanol filtered through buchner funnel. AS
11:50 - Hexane filtered through buchner funnel. CT
11:52 - Acetone filtered through buchner funnel. CT
11:54 - Distilled Water filtered through buchner funnel. CT
11:58 - Glass eppendorf tubes weighed.
12:16 - 1mL of solutions: Acetonitrile, Chloroform, Methanol, Hexane, Acetone, and Distilled Water pippetted into eppendorf tubes.
12:20 - 500 microliters of THF and Ethanol pippetted into eppedorf tubes.
12:24 - Eight sample eppendorf tubes placed into speed vacuum for fast evaporation of solvent.
14:05 Removed the vials from the speed-vac....vial containing water solution still contained a small amount of water..therefore it was left in the speed-vac.
14:20 Obtained the weights of the vials after solvent evaporation.
16:30 Removed the vial containing water solution of the ugi product. The dry vial was weighed.
18:20 To confirm the results of trial#1 for Acetonitrile, THF, methanol and ethanol, trial#2 runs were conducted. To this effect 4 vials labeled with respective solvent were made, to these vials plenty of the ugi product was added until the solutions turned turbid. The vials were capped and left in the hood.
2008-08-20
15:00 Filtered the solutions, weighed four 0.5dram sample vial (dry) placed 1mL in of the previously filtered solutions in the vials and set them in a speed-vac
15:25 Removed from the speed-vac..obtained weights of the vials again.

Tags


Compound
Inchi Key
Inchi
Methanol
OKKJLVBELUTLKV-UHFFFAOYAX
InChI=1/CH4O/c1-2/h2H,1H3
Ethanol
LFQSCWFLJHTTHZ-UHFFFAOYAB
InChI=1/C2H6O/c1-2-3/h3H,2H2,1H3
Acetonitrile
WEVYAHXRMPXWCK-UHFFFAOYAJ
InChI=1/C2H3N/c1-2-3/h1H3
Tetrahydrofuran
WYURNTSHIVDZCO-UHFFFAOYAI
InChI=1/C4H8O/c1-2-4-5-3-1/h1-4H2
Ugi adduct
BXAOUWIVXLQYOZ-UHFFFAOYAZ
InChI=1/C24H33N3O5/c1-23(2,3)26-21(29)20(17-11-8-7-9-12-17)27(16- ​18-13-10-14-31-18)19(28)15-25-22(30)32-24(4,5)6/h7-14,20H,15-16H2​ ,1-6H3,(H,25,30)(H,26,29)