Sodium Iodide → N-(4-((3-allyl-4-oxo-4,6-dihydro-3H-spiro[benzo[h]quinazoline-5,1'-cyclohexane]-2-ylthio)methyl)phenyl)acetamide

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A mixture of 3-allyl-2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1′-cyclohexan]-4(6H)-one (5, 0.100 g, 0.295 mmol), 4-acetamidobenzyl chloride (0.060 g, 0.325 mmol), potassium hydroxide (0.025 g, 0.443 mmol), and catalytic sodium iodide (4.43 mg, 0.030 mmol) in ethanol (1.738 ml) was refluxed for 24 h. 1 ml of water was added to the cooled reaction and the mixture was extracted with EtOAc 2×. The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.95, 8.10, 7.51, 7.39-7.32, 5.85, 5.20, 5.13, 4.59-4.56, 3.02, 2.02, 1.70-1.67, 1.60-1.50, 1.28; MS (EI) m/z 486 (M+1)

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