TRIS(2-BENZIMIDAZOLYLMETHYL)AMINE) synthesis

Yield: 93%

Reaction Conditions:

in ethylene glycol at 200;

Steps:

Synthesis of (BimH)3 -“3N Ligand”
The ligands were synthesised using a modified version of the conditions detailed by V. O. Rodionov et.al. ( J . Am. Chem. Soc., 129 (42), (2007), 12696-704). o-Phenylenediamine (4.22 g, 39 mmols), nitrilotriacetic acid (2.48 g, 13 mmols) and ethylene glycol (30 ml) were all added to an appropriate round bottom flask, which was then heated to 200°C under stirring, at which point the brown solution became purple. The reaction was left overnight under reflux using a waterless condenser. The flask was removed from the heat and left to cool to room temperature. Once cooled, the contents were transferred to a beaker and ice water was added, forming a precipitate. The mixture was stirred for 5 minutes at room temperature, after which it was filtered in vacuo to give a pink solid. The precipitate was left to dry overnight. The crude product was recrystallized from ethanol and left to dry in air, affording a pure peach solid. Yield 93%. dH/ppm (400 MHz, DMSO) 12.45 (s, 3H), 7.57 (m, 6H), 7.17 (m, 6H), 4.15 (s, 6H); m/z (ES-ToF); (0331) 408.19 ([M+H]⁺).

References:

IMPERIAL COLLEGE INNOVATIONS LIMITED;BARTER, Laura;LONG, Nicholas;RAINS, Jonathan;WOSCHOLSKI, Rudiger WO2020/89630, 2020, A1 Location in patent:Paragraph 0190-0191