IMidazole epoxy catalyst, ECAT-243 synthesis

Yield: 99.9%

Reaction Conditions:

in toluene for 1.36667 h;Inert atmosphere;Reflux;

Steps:

Example 13 Synthesis of Compound 13 [0227] [0228] A 2-neck, 100 ml flask was charged with 1-(3-aminopropyl)imidazole (12.5 g, 100 mmol), 2′-hydroxyacetophenone (13.6 g, 100 mmol), and toluene (50 ml). A significant exotherm was noticed when the components were first mixed at room temperature. A stir bar was added and a temperature controller, 25 ml Dean-Stark trap, condenser, and bubbler were attached. The mix was stirred and refluxed at 120° C. under an argon blanket for 7.5 hours. A total of 1.7 ml of H₂O was collected in the trap. The temperature was reduced to 110° C. and the mixture was sparged with argon for 35 minutes. The product turned into a yellow solid upon cooling. The yield was 24.3 grams, 99.9% of theory. [0229] A TGA was run on the compound and it was found to have a retained weight at 200° C. (ramp rate=10° C./min., air purge) of 96.9% and a decomposition onset at 238.2° C. An infrared spectrum on the compound included prominent absorptions at 3072, 1613, 1564, 1510, 1445, 1396, 1240, 1109, 1074, 994, 856, 769, 732, and 670 wavenumbers.

References:

DESIGNER MOLECULES, INC.;Dershem, Stephen M US2013/12620, 2013, A1 Location in patent:Paragraph 0228