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

Participants

Reaction Steps

A mixture of 3-allyl-2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1′-cyclohexan]-4(6H)-one (5, 0.100 g, 0.295 mmol), 2-Methoxyethyl p-Toluenesulfonate (0.084 ml, 0.325 mmol), potassium hydroxide (0.025 g, 0.443 mmol) in Ethanol (1.738 ml) was refluxed ON. To the cooled solution, water (1 ml) was added and the mixture was extracted with EtOAc 2×. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated to a yellow oil. The product was purified by flash column chromatography eluting with 0 to 2.5% EtOAc in hexane. 1H NMR (500 MHz, CDCl3) δ ppm 8.08, 7.39-7.23, 5.95, 5.33-5.28, 4.71, 3.79, 3.57, 3.45, 3.06, 2.61, 1.75-1.72, 1.60-1.54, 1.42-1.39; MS (EI) m/z 397 (M+1)

Provenance & Evidence