2533-69-9, These common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To the solution containing 4,5-diaminobenzo-15-crown-5 prepared in the last step, methyl 2,2,2-trichloroacetimidate (90 L, 0.70 mmol) was added. The mixture was stirred at rt shielded from light. After 9h, K2CO3 (6.0 g) was added to the mixture. The mixture was stirred for 11 h. The solvent was evaporated to give brown solid. Deionized water (70 mL) was added to the solid, and the mixture was stirred at rt for 5 h. The precipitate was filtered on Celite 545 mu, and washed with deionized water. The precipitate was eluted with a mixture of CHCl3/MeOH (1/1). The solution was concentrated under reduced pressure to give light brown solid, which was passed through a short alumina column chromatography by using a mixture of CHCl3/MeOH (10/1) as an eluent. The fractions were concentrated, and the residue was recrystalized from acetic acid to give 1 (104 mg, 21%) as pale yellow crystal. HRMS (FAB) m/z ([M + Na]+) 637.2486, calcd for C30H38N4O10Na 637.2486. 1H NMR (600 MHz, CDCl3): 7.05 (s, 4H, Ar), 3.96 (br, 8H, crown), 3.86 (br, 8H, crown), 3.75 (br, 16H, crown); 13C NMR (150 MHz, CDCl3): 148.19 (C), 142.92 (C), 133.03 (C), 99.26 (CH), 70.81 (CH2), 70.15 (CH2), 69.22 (CH2), 69.07 (CH2).
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2533-69-9.
Reference:
Article; Satake, Akiharu; Tanaka, Kazuo; Asakura, Hiroki; Okano, Masahiro; Hashimoto, Tsutsumu; Matsuura, You; Inaba, Yusuke; Oda, Tetsuhisa; Hirota, Shun; Koshino, Hiroyuki; Bulletin of the Chemical Society of Japan; vol. 87; 1; (2014); p. 88 – 97;,
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