Hexane → 4-(Phenylethynyl)-1,3-thiazol-2-amine

참여 물질

반응 단계

1-Chloro-4-phenyl-3-butyn-2-one (245 mg, 1.37 mmol) was dissolved in DMF (1.0 mL), thiourea (126 mg, 1.66 mmol) was added, and the resulting pale brown solution was stirred at ambient temperature for 5 days. The reaction mixture was diluted with Ethyl acetate (50 mL), washed with saturated NaHCO3 solution (10 mL), water (10 mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The dark oil was dissolved in methanol, adsorbed onto silica gel and purified by column chromatography eluting with 4:1, 3:1, then 2:1 hexane:ethyl acetate to afford 4-(phenylethynyl)-1,3-thiazol-2-amine (56 mg, 20% yield) as an oil. 1H NMR (CDCl3, 300 MHz) δ 7.53–7.50 (m, 2H), 7.37–7.32 (m, 3H), 6.77 (s, 1H), 5.41 (br s, 2H). MS (EI ionization) 200 (M+).

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