Sodium Iodide → HCID 18008958, compound

Participants

Reaction Steps

A mixture of methanesulphonic acid 2-[benzyl-(4-bromo-2-nitro-phenyl)-amino]-ethyl ester (25 g, Reference Example 8) and sodium iodide (16.23 g) in anhydrous acetone (100 ml) was heated at reflux for 4 hours when a further portion of sodium iodide (8.12 g) was added and refluxing was continued for a further 16 hours. The reaction mixture was evaporated under reduced pressure (2.7 kPa) at 40° C. and the residue was treated with distilled water (200 ml). The resulting mixture was extracted three times with dichloromethane (150 ml). The combined organic extracts were dried over magnesium sulphate and then evaporated under reduced pressure (2.7 kPa) at 40° C. The resulting brown oil (29,16 g) was subjected to flash chromatography on silica (0,040-0,063 mm) eluting with a mixture of cyclohexane and ethyl acetate (9:1, v/v) to give the title compound (23.55 g) as a yellow oil. 1H NMR, 300 HMz, (CD3)2SO: δ3.3 (m, 4H); 4.4 (s, 2H); 7.25(m, 5H); 7.4 (d, J=8 Hz, 1H); 7.6 (dd, J=8 Hz and J=1.5 Hz, 1H); 8 (d, J=1.5 Hz, 1H). MS (EI): M+ 462 and 460 (5%), 445 and 443 (20%), 321 and 319 (10%), 91 (100%).

Provenance & Evidence