Benzoyl chloride → N-[6-Methoxyquinol-5-yl]thiourea

Beteiligte Stoffe

Reaktionsschritte

1.7 g or ammonium thiocyanate are dissolved in 50 ml of acetone, 2.5 ml of benzoyl chloride are then added and the reaction mixture is heated at reflux for 15 minutes. 2.9 g of amine (Compound 14), dissolved in 20 ml of acetone, are added and the reaction mixture is then heated to reflux for 30 minutes. Evaporation is carried out to dryness and the residue is taken up in water and then extracted with ethyl acetate. The residue is deprotected by treatment with 5 ml of 33% ammonia in 10 ml of ethanol at reflux for 2 hours. The precipitate formed is separated off by filtration, the filtrate is evaporated and the residue is triturated with a 75/25 (v/v) ethyl acetate/hexane mixture, to obtain 3.5 g of white powder. 1H NMR (CDCl3): 3.93 (s, 3H, --OCH3), 7.50-7.53 (m, 1H, H3), 7.70 (d, 1H, J=9.5, 1H, H7), 8.00 (d, J=9.5, 1H, H4), 8.08 (d, 1H, H8), 8.75 (d, J=2.5, 1H, H2).

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