Water → HCID 53866075, compound

Participants

Reaction Steps

A solution of 2-[benzyl-(4-bromo-2-nitro-phenyl)-amino]-ethanol (19.52 g, Reference Example 9) and triethylamine (7.8 ml) in anhydrous tetrahydrofuran (95 ml), at 25° C., was treated dropwise with methanesulphonyl chloride (4.75 ml). After stirring for 4 hours at 25° C. a further portion of methanesulphonyl chloride (4.75 ml) was added and stirring was continued for a further 16 hours at 25° C. The reaction mixture was treated with water (100 ml), the organic phase was separated and the aqueous phase was extracted three times with ethyl acetate (150 ml). The combined organic phases were washed with saturated aqueous sodium hydrogen carbonate solution (50 ml), then three times with distilled water (50 ml), then dried over magnesium sulphate and then evaporated under reduced pressure (2.7 kPa) at 40° C. to give the title compound (25.41 g) as a brown oil. 1H NMR, 300 MHz, (CD3)2SO: δ3.1 (s, 3H); 3.4 (t, 2H); 4.2 (t, 2H); 4.4 (s, 2H); 7.2(m, 5H); 7.4 (d, J=8 Hz, 1H); 7.7 (dd, J=8 Hz and J=1.5 Hz, 1H); 8 (d, J=1.5 Hz, 1H). MS (EI): M+ 430 and 428 (5%), 321 and 319 (20%), 91 (100%).

Provenance & Evidence