Benzoic acid, 2-amino-5-iodo- → 6-Iodo-2-trichloromethyl-1,2-dihydro-quinazolin-4-one

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Reaction Conditions

Reaction Steps

To a solution of 5-iodoanthranilic acid (131.5 g, 500 mmol) in ethanol (700 mL), 2,2,2-trichloroacetimidate (88.2 g, 500 mmol) was added. The reaction mixture was heated at 45° C. for 3 days under stirring. The solid formed was filtered and washed with fresh ethanol and air-dried. Yield 129.51 g (66.4%). Mp 224°-225° C. 1H-NMR (DMSO) 7.59 (d, 1h, J=8.6 Hz), 8.21 (dd, 1H, J=2 Hz, J=7.5 Hz), 8.44, 1H, J=1.9 Hz), 13.55 (bs, 1H). MS(CI); M+ =499. CHN calculated for C16H18 Cl3IN4.HCl; C: 35.84, H: 3.57, N: 10.45; Found: C: 35.81, H: 3.35, N: 10.44.

Provenance & Evidence