Triethylamine → 2,3-Dihydro-6-iodo-3-propyl-2-thioxo-4(1H)-quinazolinone

Participants

Reaction Steps

To a slurry of 2-amino-5-iodobenzoic acid (100 g, 0.38 mol) in n-propyl acetate (315 mL) was added triethylamine (58 mL, 0.42 mol) at room temperature. The resulting solution was heated to reflux and n-propyl isothiocyanate (43 mL, 0.42 mol) was added over a one hour period. The reaction mixture was maintained at reflux for 18 h, then cooled to room temperature and filtered. The wetcake was washed with fresh propyl acetate and dried at 60° C. under vacuum. In this manner, 113 g of the title compound was obtained as a tan solid. m.p.>200° C.; 1H NMR (Me2SO--d6): δ13.02 (bs,1H), 8.22 (d,1H), 8.06 (dd,1H), 7.21 (d,1H), 4.34 (m,2H), 1.69 (m,2H), 0.93 (t,3H).

Provenance & Evidence