p-Toluenesulfonic acid → BAS 00699730

Participants

Reaction Steps

Isatoic anhydride (163 mg, 10 003|\ was dissolved under an argon atmosphere in 5 ml of ethanol and, after addition of 4-chlorobenzaldehyde (211 mg, 15 mmol), ammonium acetate (93 mg, 12 mmol) and 4-toluenesulfonic acid (86 mg, 5 mmol), boiled at reflux for 5 hours. The product precipitated in the course of cooling. The precipitated solid was washed with a little ethanol and dried. This gave 150 mg (54.5% of theory) of 2-(4-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one as a white solid of melting point 190° C. 1H NMR (400 MHz, CDCl3 δ, ppm) 7.95 (d, 1H), 7.55 (dd, 2H), 7.42 (dd, 2H), 7.34 (t, 1H), 6.91 (t, 1H), 6.68 (d, 1H), 5.90 (s, 1H), 5.75 (br. S, 1H), 4.35 (br. S, 1H).

Provenance & Evidence