Benzaldehyde → 1-isopropyl-4-phenyl-6,7-methylenedioxy-3,4-dihydro-2(1H)-quinazolinone

HRID 1973432Notes

Reaction equation

HRID 1973432 reaction equation
[CH:1]([N:4]([C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[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.C1(C)C=CC=CC=1.C>CS(O)(=O)=O.C(O)CC>[CH:1]([N:4]1[C:8]2[C:13](=[CH:12][C:11]3[O:14][CH2:15][O:16][C:10]=3[CH:9]=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

7

Reactant 4

HCID 240BenzaldehydeHCID 297MethaneHCID 1140TolueneHCID 1005551-(1,3-Benzodioxol-5-yl)-1-isopropylurea

Product 1

HCID 127894691-isopropyl-4-phenyl-6,7-methylenedioxy-3,4-dihydro-2(1H)-quinazolinone

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 10311-PropanolSolvent

Procedure

A solution of 10.3 gm. of N-isopropyl-(3,4-methylenedioxyphenyl)urea, 7.1 ml. of benzaldehyde, and 3 drops of methanesulphonic acid in 250 ml. of toluene is refluxed under a water separator for 21 hours. The cooled solution is then washed with 200 ml. of water, dried and evaporated to yield a powder. This product is decolorized in hot propanol with a small amount of activated charcoal and recrystallized from propanol to obtain 1-isopropyl-4-phenyl-6,7-methylenedioxy-3,4-dihydro-2(1H)-quinazolinone, m.p. 169°-172°C.

Workup

  1. washThe cooled solution is then washed with 200 ml
  2. dry with materialof water, dried
  3. customevaporated
  4. customto yield a powder
  5. customrecrystallized from propanol

Sources & evidence

ORD record
ord-8bd7f384ee8841eb8f343841c2fa2646
Source dataset
uspto-grants-1976_12
Patent number
US03997564

Reaction notes

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