Synthesis
GENERAL METHOD: 2-formylthiazole (54 mg, 0.5 mmol) and ammonium acetate (385 mg, 5.0 mmol) were dissolved in acetonitrile (6 mL) at room temperature, followed by the addition of trimethylphenyltrimethylammonium (376 mg, 1.0 mmol). The reaction mixture was stirred at room temperature for 21 h. The reaction mixture was sequentially treated with 0.5 M Na2S2O3 aqueous solution (10 mL) and 1.0 M NaHCO3 aqueous solution (15 mL), and then extracted with ethyl acetate (60 mL). The organic layer was washed sequentially with 0.5 M Na2S2O3 aqueous solution and saturated NaCl aqueous solution, and finally dried with anhydrous MgSO4.
References
[1] Heterocycles, 2016, vol. 92, # 10, p. 1796 - 1802
[2] Patent: EP1555257, 2005, A1. Location in patent: Page/Page column 25
[3] Tetrahedron Letters, 2013, vol. 54, # 17, p. 2177 - 2179
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 3, p. 496 - 500
