2-Bromo-1-(2-chloro-4-methoxyphenyl)-propan-1-one → 4-(2-Chloro-4-methoxyphenyl)-5-methyl-2-(N-naphth-1-yl-N-propylamino)thiazole

Participants

Reaction Steps

A solution containing 0.5 g of N-naphth-1-yl-N-propylthiourea and 0.5 g of 2-bromo-1-(2-chloro-4-methoxyphenyl)propan-1-one in 15 ml of methanol is heated at reflux for 6 hours. The reaction mixture is then evaporated to dryness and then, successively, the residue is taken up in water, basified with 33% sodium hydroxide and extracted with ethyl acetate and the organic phase is dried over sodium sulphate, filtered and concentrated under vacuum. The residue is then purified on a column of silica gel eluted with ethyl acetate, to provide 0.56 g of a yellow oil. 1H NMR (CDCl3): 0.97 (t, J=7.7, 3H, --CH2 --CH3), 1.73 (sex, 2H, --CH2 --CH3), 2.04 (s, 3H, --CH3), 3.82 (s, 3H, --OCH3), 3.90 (m, 2H, --CH2 --CH2 --CH3), 6.89 (dd, J=1.8, J=8.0, 1H, H5arom) 7.02 (d, J=1.8, 1H, H3arom), 7.50-7.70 (m, 4H, H2, H3, H8 and H6arom), 7.85-8.10 (m, H, H6, H7, H4 and H5).

Provenance & Evidence