Hydrogen Bromide → HCID 10791123, compound

Participants

Reaction Steps

In acetic acid (5 ml) was dissolved 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-[3-[N-methyl-N-[2-(3,4-methylenedioxyphenoxy)ethyl]amino]propyl]-1,3-thiazolidin-4-one (0.35 g), and 47% hydrobromic acid (5 ml) was added, then the mixture was stirred at room temperature for 7 days. After completion of the reaction, the mixture was poured into an ice-cooled 5% aqueous solution of sodium carbonate and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform-methanol, 98:2) to afford 0.05 g (16%) of the title compound as a pale brown oil. NMR (CDCl3) (200 MHz) δ: 1.37 (9H, s), 1.2-1.9 (2H, m), 2.26 (3H, s), 2.1-2.5 (2H, m), 2.71 (2H, t, J=5.7 Hz), 2.6-3.0 (1H, m), 3.4-3.8 (1H, m), 3.67 and 3.80 (2H, ABq, J=16.0 Hz), 3.94 (2H, t, J=5.7 Hz), 5.60 (1H, s), 5.82 (1H, s), 5.88 (2H, s), 6.1-7.0 (5H, m), 7.14 (1H, s)

Provenance & Evidence