Crystal structure of (E)-N,N-diethyl-2-(5-nitrothiazol-2-yl)-1-phenylethen-1-amine, C₁₅H₁₇N₃O₂S

Abstract

CCDC no.: 1558756The title crystal structure is shown in the figure. conditions. Table 2 lists the atoms with their coordinates and displacement parameters. Source of materialsThe title compound was synthesized from the Sonogashira Coupling-Aminovinylation Sequence reaction [4]. In a nitrogen atmosphere, a THF solution of phenylacetylene (1.1 mmol in 5 mL THF) was added dropwisely into a stirred mixture of 2-bromo-5-nitrothiazole (1 mmol), Pd(PPh 3 ) 2 Cl 2 (14 mg, 0.02 mmol), CuI (7 mg, 0.04 mmol), and 11 mL of THF/NEt 3 (10:1). The reaction mixture was stirred at room temperature overnight until conversion was complete (monitored by TLC). Then, a solution of diethylamine (2 mmol) in 5 mL of methanol was added, and the mixture was heated to reflux for ca. 9 hour until complete conversion (monitored by TLC). The solvents were evaporated in vacuo, and the residue was purified by chromatography over a short pad of aluminum oxide eluting with dichloromethane followed by acetone to yield 60% of the entitled compound. The residue was then recrystallized in dichloromethane by evaporation in vacuo, which yielded dark red crystals. After several attempts a suitable crystal for single X-ray diffraction study was obtained. Experimental detailsH atoms were fixed geometrically at ideal positions and allowed to ride on the parent atoms with C-H = 0.93-0.97 Å, with U iso (H) = 1.5Ueq(C) (for CH 3 )and 1.2 Ueq(C) (for CH 2 and CH).