Benzaldehyde → 1-isopropyl-4-phenyl-3,4,6,7-tetrahydro-furo[3,2-g] quinazolin-2(1H)-one

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Reaction Steps

A solution of 8.0 g. of 1-Isopropyl-1-(2,3-dihydro-6-benzofuranyl)urea, 3.6 ml. of benzaldehyde, 5 drops of methanesulfonic acid and 200 ml. of toluene is stirred and refluxed under a water separator for 20 hours. The resulting solution is cooled and the cooled solution is washed twice with 150 ml. water, dried with anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue is dissolved in a minimum amount of chloroform and chromatographed on silica gel (200 g.) using chloroform as an eluent to give an oil of 1-isopropyl-4-phenyl-3,4,6,7-tetrahydro-furo[3,2-g] quinazolin-2(1H)-one and an oil of 6-isopropyl -9-phenyl-2,3,8,9-tetrahydro-furan[2,3-f]quinazolin-7(6H)-one.

Provenance & Evidence