Chemical Properties
off-white to white powder
Uses
Phthalimidoacetaldehyde diethyl acetal is used as a pharmaceutical intermediate.
Synthesis
The general procedure for the synthesis of benzoyliminoacetaldehyde diethyl acetal from potassium phthalimide salt and bromoacetaldehyde diethyl acetal was as follows: potassium phthalimide (5 g, 26.5 mmol), bromoacetaldehyde diethyl acetal (4.1 mL, 26.5 mmol), and cetyltributylphosphonium bromide (13.8 g, 26.5 mmol) were reacted under nitrogen protection in toluene ( 200 mL) at 111°C for 24 hours under nitrogen protection. After completion of the reaction, the mixture was filtered and the filtrate was concentrated by rotary evaporation to give a yellow oil. The target compound was purified by column chromatography (eluent: hexane/ether=1:1). The yield was 70%. Elemental analysis results (calculated value C14H17NO4, 263.29): C 63.8, H 6.4, N 5.3; measured value: C 64.6, H 6.5, N 5.3. 1H NMR (300MHz, CDCl3): δ7.8-7.6 (m, 4H), 4.79 (t, 1H), 3.75 (d, 2H), 3.62-3.42 (m, 4H), 1.06 (t, 6H).ES-MS: m/z 264.IR: ν(C-O-C) 2800, (C=O) 1721 cm-1.
References
[1] Russian Journal of General Chemistry, 2007, vol. 77, # 1, p. 98 - 102
[2] Journal of Chemistry, 2015, vol. 2015,
[3] Patent: WO2017/32840, 2017, A1. Location in patent: Page/Page column 264; 265
[4] Journal of Pharmacy and Pharmacology, 1952, vol. 4, p. 693,705
