2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3-[(8-Phenylthieno[2,3-h]quinazolin-2-yl)amino]benzenesulfonamide

Participants

Reaction Steps

To a dark solution of 3-(8-Phenyl-5,6-dihydro-thieno[2,3-h]quinazolin-2-ylamino)-benzenesulfonamide (130 mg, 0.30 mmol) in anhydrous 1,4-dioxane (7 mL) was added DDQ (75 mg, 0.33 mmol) and the mixture was refluxed under nitrogen for 2-3 hours. The reaction mixture was concentrated in vacuo and the resulting crude residue was triturated in a mixture of 2M NaOH (25 mL) and DCM (25 mL). The resulting solid was filtered and washed with DCM and water to afford 50 mg (39% yield) of the title compound as a pale yellow/green powder. MS (ES+) 433, (ES−) 431. δH (d6 DMSO) 7.39 (2H, br s), 7.41 (1H, m), 7.51 (4H, br m), 7.72 (1H, d), 7.83 (1H, d), 7.96 (3H, m), 8.68 (1H, s), 9.40 (1H, s), 9.61 (1H, br s) and 10.41 (1H, s).

Provenance & Evidence