Some common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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. Product Details of 61881-19-4
3.1.7 Methyl 4-O-acetyl-2,3-di-O-benzyl-alpha-d-galactopyranosiduronate 1-N-phenyltrifluoroacetimidate (7) Compound 17 (2.40 g, 5.4 mmol) was dissolved in AcOH (90 mL) and Ac2O (90 mL). The reaction mixture was cooled in an ice bath for 10 min, H2SO4 (0.9 mL) was then slowly added. The reaction was monitored by TLC (petroleum ether/ethyl acetate, 2:1) and showed completion after approximately 3 h. The reaction mixture was allowed to warm to rt during the progress of the reaction. NaOAc (9.2 g) was added and the mixture was stirred until all NaOAc had dissolved. The mixture was then evaporated to dryness, taken up in EtOAc, washed with H2O (extracted with EtOAc), dried over Na2SO4, filtered, evaporated to dryness, and finally co-evaporated three times with EtOH. The resulting syrup was purified by chromatography on silica gel (petroleum ether/ethyl acetate, 3:1) to provide a white solid (2.37 g, 93%, alpha and beta isomers were not separable). Ammonia gas was bubbled through a solution of the above product (2.16 g, 4.6 mmol) in a mixture of THF/CH3OH (v/v, 7: 3, 45 mL) cooled in an ice bath for 20 min. The solvent was then concentrated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 2:1) to afford 18 (1.48 g, 75%) as a white solid. A suspension of hemiacetal 18 (472 mg, 1.1 mmol), K2CO3 (455 mg, 3.3 mmol), and N-phenyl trifluoroacetimidoyl chloride (457 mg, 2.2 mmol) in acetone (6.6 mL) was stirred at ambient temperature for 2 h. TLC showed the completion of the reaction. The mixture was filtered and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 7:1) to afford 7 (570 mg, 87%), which was used directly without characterization.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 61881-19-4, its application will become more common.
Reference:
Article; Ma, Yuyong; Cao, Xin; Yu, Biao; Carbohydrate Research; vol. 377; (2013); p. 63 – 74;,
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