1-(4-Me-Phenyl)-imidazole (2.00 g, 12.7 mmol) and 2-chloro-N-(2,6-Me2-phenyl)acetamide (2.76 g, 14.0 mmol)
were refluxed in toluene (ca. 25 mL) for 12 h, after which the reaction
mixture was cooled to 30 °C. The formed solid was filtered off
and washed repeatedly with diethyl ether to give the crude product,
which was purified by column chromatography on neutral silica using
CHCl3/CH3OH (9.5:0.5 v/v) mixed medium to give
the product (1a) as a light brown solid (1.86 g, 41%). 1H NMR (CDCl3, 500 MHz, 25 °C): δ, 10.48
(s, 1H, NCHN), 10.1 (s, 1H,
NH), 7.81 (s, 1H, NCHCHN), 7.42 (s, 1H, NCHCHN), 7.35 (d, 2H, 3JHH = 8 Hz, 4-(CH3)C6H4), 7.18 (d, 2H, 3JHH = 8 Hz, 4-(CH3)C6H4), 6.9 (t, 1H, 3JHH = 6 Hz, 2,6-(CH3)2C6H3), 6.84 (d, 2H, 3JHH = 7 Hz, 2,6-(CH3)2C6H3), 5.71 (s, 2H, CH2), 2.29 (s, 3H, 4-(CH3)C6H4), 2.10
(s, 6H, 2,6-(CH3)2C6H3). 13C{1H} NMR (CDCl3, 125 MHz, 25 °C): δ ppm, 163.6
(CO), 140.7 (4-(CH3)C6H4), 135.9 (NCHN), 135.3 (2,6-(CH3)2C6H3), 133.6 (4-(CH3)C6H4), 132 (2,6-(CH3)2C6H3), 130.9 (4-(CH3)C6H4), 127.9 (2,6-(CH3)2C6H3), 127.1 (2,6-(CH3)2C6H3), 124.6
(NCHCHN), 121.6 (4-(CH3)C6H4), 120.2 (NCHCHN),
51.9 (CH2), 21.1
(4-(CH3)C6H4), 18.7 (2,6-(CH3)2C6H3). IR data (cm–1) KBr pellet: 3406 (m), 3253 (m), 3049 (m), 1671 (s),
1547 (s), 1471 (m), 1441 (w), 1267 (w), 1239 (m), 1073 (w), 819 (w),
763 (w), 514 (w). HRMS (ESI): Calcd. for [M – Cl]+, [C20H22N3O]+m/z 320.1757; found m/z 320.1755. Anal. Calcd. for C20H22N3OCl: C, 67.50; H, 6.23; N, 11.81; Found: C, 67.20; H,
6.413; N, 11.57%.
Prakasham A.P., Patil S.K., Nettem C., Dey S., Rajaraman G, & Ghosh P. (2023). Discrete Singular Metallophilic Interaction in Stable Large 12-Membered Binuclear Silver and Gold Metallamacrocycles of Amido-Functionalized Imidazole and 1,2,4-Triazole-Derived N-Heterocyclic Carbenes. ACS Omega, 8(7), 6439-6454.