Synthesis
General procedure for the synthesis of N-propargyl phthalimide from phthalimide potassium salt and 3-bromopropargyl: 8.4 mmol of 3-bromopropargyl and 8.4 mmol of phthalimide potassium salt were dissolved in 10 mL of N,N-dimethylformamide. Subsequently, 0.2 g of manganese dioxide solid was added as a catalyst. The reaction mixture was stirred at 28°C for 2 hours. Upon completion of the reaction, the mixture was diluted by adding 100 mL of ethyl acetate to the mixture, followed by washing with water to collect the organic layer. The organic layer was further washed with saturated aqueous sodium chloride solution and dried with anhydrous sodium sulfate. The dried organic phase was separated and purified by column chromatography with the eluent being a solvent mixture of petroleum ether and ethyl acetate (5:1, v/v) to obtain pure N-propargyl phthalimide.
References
[1] Patent: CN105669525, 2016, A. Location in patent: Paragraph 0062; 0063; 0082
[2] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2002, vol. 377, p. 13 - 18
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2004, vol. 179, # 8, p. 1611 - 1614
[4] Patent: WO2005/82892, 2005, A2. Location in patent: Page/Page column 58-59
[5] European Journal of Organic Chemistry, 2017, vol. 2017, # 27, p. 3941 - 3946
