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Ethyl 2-[[2-(3-nitrophenyl)-5-phenyl-1H-imidazol-4-yl]sulfanyl]acetate: synthesis via a microwave-mediated
John F Gallagher1, Clare M Coleman, Donal F O'Shea
1School of Chemical Sciences, Dublin City University, Dublin 9, Ireland. john.gallagher@dcu.ie
Abstract:
The orange title compound, C(19)H(17)N(3)O(4)S, can be synthesized either via microwave-mediated combinatorial chemistry strategies or conventional synthetic procedures. The phenyl and meta-nitrophenyl C(6) rings are essentially coplanar with the central imidazolyl ring, with interplanar angles of 0.87 (5) and 0.97 (4), respectively, resulting in optimum conjugation (SCH(2) moiety included); lambda(max) = 281 nm in CH(3)CN. The principal intermolecular interactions are N(imid)-H...O(nitro) and N(imid)-H...O[double bond]C [N...O = 3.058 (2) and 3.432 (3) A, and N-H...O = 128 and 153, respectively]. The closest H.S distance is an intramolecular C-H...S contact, with H...S = 2.54 A and C-H...S = 136.