Exp226

Reactants
media type="custom" key="3855401"media type="custom" key="3855409"media type="custom" key="3855423"media type="custom" key="3856399"media type="custom" key="3856407"media type="custom" key="3856421"media type="custom" key="3856425"media type="custom" key="3856435"media type="custom" key="3856447"media type="custom" key="3856461"media type="custom" key="3856471"

Solvent
media type="custom" key="3856479"

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

UC226-3 Predicted Ugi Product:

UC226-4 Predicted Ugi Product:

UC226-5 Predicted Ugi Product:

UC226-6 Predicted Ugi Product:

UC226-7 Predicted Ugi Product:

UC226-8 Predicted Ugi Product:

Objective
To synthesis eight different Ugi products.

Procedure

 * Label || Amount of Solution of [|Benzaldehyde], [|5-Methyl furfurylamine], and [|1-Pyrene butanoic acid]with [|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 ||

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]** media type="googlespreadsheet" key="rDsL3ghZGO3vfCAw6Yo3izg" height="400" width="900"
 * 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 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 16:20 Added isocyanides 17.38 Weighed vials 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
 * 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 ||
 * 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 ||
 * 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 ||
 * 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 ||

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