Water → 3-allyl-2-(3-methoxybenzylthio)-3H-spiro[benzo[h]quinazoline-5,1'-cyclohexan]-4(6H)-one

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Reaction Steps

A mixture of 3-allyl-2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1′-cyclohexan]-4(6H)-one (5, 0.075 g, 0.222 mmol), 3-methoxybenzyl bromide (0.034 ml, 0.244 mmol), potassium hydroxide (0.019 g, 0.332 mmol) in Ethanol (1.303 ml) was refluxed overnight. To the cooled solution, water (1 ml) was added and the product was extracted with 10% MeOH in EtOAc, dried over sodium sulfate, and concentrated. The title compound was purified by flash column chromatography, eluting with 0 to 5% EtOAc in hexane. 1H NMR (500 MHz, CDCl3) δ ppm 8.15, 7.38-7.23, 7.06-7.02, 6.86-6.84, 5.945.32, 5.32-5.27, 4.69, 4.59, 3.77, 3.06, 2.60, 1.75-1.72, 1.60-1.54, 1.43-1.37; MS (EI) m/z 459 (M+1)

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