US 12,077,520 B2
Compounds for the selective solid-liquid extraction and liquid-liquid extraction of lithium chloride
Jonathan L. Sessler, Austin, TX (US); Qing He, Austin, TX (US); and Sung Kuk Kim, Jinju-si (KR)
Assigned to Board of Regents, The University of Texas System, Austin, TX (US); and GYEONGSANG NATIONAL UNIVERSITY, Jinju-si (KR)
Appl. No. 17/057,713
Filed by BOARD OF REGENTS, THE UNIVERSITY OF THE TEXAS SYSTEM, Austin, TX (US); and GYEONGSANG NATIONAL UNIVERSITY, Jinju-si (KR)
PCT Filed May 23, 2019, PCT No. PCT/US2019/033690
§ 371(c)(1), (2) Date Nov. 23, 2020,
PCT Pub. No. WO2019/226863, PCT Pub. Date Nov. 28, 2019.
Claims priority of provisional application 62/675,558, filed on May 23, 2018.
Prior Publication US 2022/0274956 A1, Sep. 1, 2022
Int. Cl. C07D 401/14 (2006.01); B01D 11/04 (2006.01); C01D 15/04 (2006.01); C07D 471/04 (2006.01); C22B 3/16 (2006.01); C22B 3/36 (2006.01); C22B 26/12 (2006.01)
CPC C07D 401/14 (2013.01) [B01D 11/0492 (2013.01); C01D 15/04 (2013.01); C07D 471/04 (2013.01); C22B 3/1666 (2013.01); C22B 3/36 (2021.05); C22B 26/12 (2013.01)] 19 Claims
 
1. A compound of the formula:

OG Complex Work Unit Chemistry
wherein:
R1, R1′, R2, R2′, R3, R3′, R4, and R4′ are each independently hydrogen, hydroxy, amino, cyano, or halo; or
alkyl(C≤6), alkenyl(C≤6), alkynyl(C≤6), acyloxy(C≤6), alkoxy(C≤6), alkylamino(C≤6), dialkylamino(C≤12), amido(C≤6), or a substituted version of any of these groups; or
one of these groups is attached to a solid support or a fluorophore;
R5, R5′, R6, R6′, R7, and R8 are each independently hydrogen or alkyl(C≤12), cycloalkyl(C≤12), cycloalkenyl(C=12), alkenyl(C≤12), alkynyl(C≤12), aryl(C≤12), heteroalkyl(C≤12), heterocycloalkyl(C≤12), alkoxy(C≤12), alkylamino(C≤12), dialkylamino(C≤18), amido(C≤12), or a substituted version of any of these groups; or one of these groups is attached to a solid support or a fluorophore;
R9, R10, R11, and R12 are hydrogen, alkyl(C≤6), or substituted alkyl(C≤6);
L and L′ are taken together and form a group of the formula:

OG Complex Work Unit Chemistry
wherein:
X and X′ are each independently alkanediyl(C≤8), cycloalkanediyl(C≤8), alkenediyl(C≤8), alkynediyl(C≤8), arenediyl(C≤8), or a substituted version of any of these groups;
Y and Y′ are each independently —O—, —C(O)—, —C(O)O—, —S(O)—, —S(O)2O—, —C(O)NRa—, or —S(O)2NRb—, wherein:
Ra and Rb are each independently hydrogen, alkyl(C≤6), or substituted alkyl(C≤6); or one or more of these groups is attached to a solid support or a fluorophore;
Z is a group of the formula:

OG Complex Work Unit Chemistry
wherein:
A1 and A1′ are each independently arenediyl(C≤8), substituted arenediyl(C≤8), heteroarenediyl(C≤8) or substituted heteroarenediyl(C≤8); and
A2 is heteroarenediyl(C≤8) or substituted heteroarenediyl(C≤8); or
Z is arenediyl(C≤24), substituted arenediyl(C≤24), heteroarenediyl(C≤24), or substituted heteroarenediyl(C≤24), wherein the group comprises at least 3 fused rings;
wherein when a chemical group is used with the “substituted” modifier, one or more hydrogen atom has been replaced, independently at each instance, by —OH, —F, —Cl, —Br, —I, —NH2, —NO2, —CO2H, —CO2CH3, —CN, —SH, —OCH3, —OCH2CH3, —C(O)CH3, —NHCH3, —NHCH2CH3, —N(CH3)2, —C(O)NH2, —C(O)NHCH3, —C(O)N(CH3)2, —OC(O)CH3, —NHC(O)CH3, —S(O)2OH, or —S(O)2NH2;
or a salt thereof.