Urea → 6-Nitro-2,4(1H,3H)-quinazolinedione

Participants

Reaction Conditions

Reaction Steps

A mixture of 5 g (27.4 mmol) of 5-nitroanthranilic acid and 22.9 g (274.0 mmol) of urea was heated to 160° C. and the melt stirred overnight. The reaction mixture was allowed to cool to 100° C. and 5 mL of water was added to dissolve the urea. The solid was filtered and suspended in 100 mL of 0.5 N NaOH and heated to boiling for 40 min to allow formation of the sodium salt. Then the mixture was cooled down and the pH was adjusted with 1 M HCl until pH=5. The precipitate was filtered off and washed with water and dried in vacuo to give 5.12 g of the title compound. 1H NMR (DMSO-d6) δ 11.7 (s, 2H), 8.6 (s, 1H), 8.45(d, 1H), 7.4 (d, 1H); LC-MS (ESI+; 208 ([M+H]+)).

Provenance & Evidence