Methyl isothiocyanate → 8-Iodo-2-mercapto-3-methylquinazolin-4(3h)-one

Participants

Reaction Conditions

Reaction Steps

A sealable flask was charged with 2-amino-3-iodobenzoic acid (Bosche Scientific; 10 g, 38.0 mmol) and methyl isothiocyanate (5.56 g, 76 mmol) in EtOH (120 mL) followed by TEA (7.93 mL, 57.0 mmol). The flask was sealed and heated in an oil bath at 100° C. for 4 h with a blast shield. The mixture was cooled to RT and the solvent was removed in vacuo. The residue was triturated with Et2O (40 mL) and filtered, dried to give 8-iodo-3-methyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (11.22 g, 35.3 mmol, 93% yield) as an off white solid. Crude material was used in the next step. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.97 (1H, br.), 8.23 (1H, d, J=8.4 Hz), 8.00 (1H, d, J=8.0 Hz), 7.15 (1H, t, J=7.5 Hz), 3.65 (3H, s).). m/z (ES, +ve) 318.8 (M+H)+.

Provenance & Evidence