Benzaldehyde → 1-isopropyl-3,4,7,8-tetrahydro-4-phenyl-furo[2,3-h]quinazolin-2(1H)-one

HRID 1658281Notes

Reaction equation

HRID 1658281 reaction equation
[CH:1]([N:4]([C:8]1[C:13]2[CH2:14][CH2:15][O:16][C:12]=2[CH:11]=[CH:10][CH:9]=1)[C:5]([NH2:7])=[O:6])([CH3:3])[CH3:2].[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CS(O)(=O)=O.C1(C)C=CC=CC=1>[CH:1]([N:4]1[C:8]2[C:9](=[CH:10][CH:11]=[C:12]3[O:16][CH2:15][CH2:14][C:13]3=2)[CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:7][C:5]1=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 21529030N-(2,3-Dihydro-1-benzofuran-4-yl)-N-propan-2-ylurea

Product 1

HCID 681363431-isopropyl-3,4,7,8-tetrahydro-4-phenyl-furo[2,3-h]quinazolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 5.0 g. of 1-isopropyl-1-(2,3-dihydro-4-benzofuranyl)urea, 3.5 ml. of benzaldehyde, 3 drops of methanesulfonic acid and 150 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 with 150 ml. water, dried with anhydrous magnesium sulfate, filtered and concentrated in vacuo to give an oil of 1-isopropyl-3,4,7,8-tetrahydro-4-phenyl-furo[2,3-h]quinazolin-2(1H)-one.

Workup

  1. temperaturerefluxed under a water separator for 20 hours
  2. temperatureThe resulting solution is cooled
  3. washthe cooled solution is washed with 150 ml
  4. dry with materialwater, dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f8a7e0db479476aba043977f594bd89
Source dataset
uspto-grants-1976_06
Patent number
US03963717

Reaction notes

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