Application of 17564-64-6, A common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, molecular formula is C9H6ClNO2, 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.
General procedure: Conditions A: aqueous 37% hydrochloric acid (0.17 mL, 2 mmol) was added to a solution of 1 (258 mg, 1.0 mmol) in 8 mL of degassed ethanol. The mixture was heated at 95 C under Argon atmosphere until the selenocarbonate 1 disappeared (2,5-3 h). After cooling to room temperature sodium bicarbonate (0.34 g, 4 mmol) and alkylhalide (1.5 mmol, see Table 3) were added and the resulting mixture was stirred until the end of the reaction (TLC analysis). After the addition of water (10 mL) the mixture was extracted three times with 10 mL of EtOAc. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified on a silica gel column with a mixture of petroleum ether and ethyl ether as eluant to give the corresponding selenide 5. Conditions B: trifluoroacetic acid (0.15 mL, 2 mmol) was added to a solution of 1 (258 mg, 1.0 mmol) in 8 mL of degassed DMF. The mixture was heated at 95 C under Argon atmosphere until the selenocarbonate 1 disappeared (2,5-3 h). After cooling to room temperature sodium acetate (0.33 g, 4 mmol) and alkyl or aryl halide (1.5 mmol, see Table 3) were added and the resulting mixture was stirred until the end of the reaction (TLC analysis). After the addition of water (10 mL) the mixture was extracted three times with 10 mL of EtOAc. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The corresponding selenide 5 was isolated after column chromatographyon SiO2 utilizing a mixture of diethyl ether and petroleum ether as eluant. Characterisation data for selenides 5b-5c [26], 5d, [27] 5e, [28] 5f [29], 5g [30], 5h [31], and 5i [32] matched the ones previously reported in literature for these compounds.
The synthetic route of 17564-64-6 has been constantly updated, and we look forward to future research findings.