3,4-Dinitrobenzaldehyde → 3-(4-sec-butylphenyl)-2-(3,4-dinitrophenyl)quinazolin-4(3H)-one

HRID 1846365Notes

Reaction equation

HRID 1846365 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[CH:7]=O)([O-:3])=[O:2].[NH2:15][C:16]1[CH:34]=[CH:33][CH:32]=[CH:31][C:17]=1[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([CH2:29][CH3:30])[CH3:28])=[CH:23][CH:22]=1)=[O:19]>CCO>[CH:27]([C:24]1[CH:25]=[CH:26][C:21]([N:20]2[C:18](=[O:19])[C:17]3[C:16](=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:15]=[C:7]2[C:6]2[CH:9]=[CH:10][C:11]([N+:12]([O-:14])=[O:13])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[CH:22][CH:23]=1)([CH2:29][CH3:30])[CH3:28]

Participants

4

Reactant 2

HCID 33622013,4-DinitrobenzaldehydeHCID 167700372-Amino-N-(4-sec-butylphenyl)benzamide

Product 1

HCID 866598193-(4-sec-butylphenyl)-2-(3,4-dinitrophenyl)quinazolin-4(3H)-oneYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Anhydrous CuCl2 (0.370 g, 2.70 mmol) and 3,4-dinitrobenzaldehyde (0.270 g, 1.38 mmol) were added to a solution of 2-amino-N-(4-sec-butylphenyl)benzamide (0.370 g, 1.38 mmol) in anhydrous EtOH (20 mL). After heating to reflux temperature for 3 hours, the mixture was concentrated in vacuo. The residue was dissolved in EtOAc, washed with H2O, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 10% to 60% EtOAc in heptane, afforded 3-(4-sec-butylphenyl)-2-(3,4-dinitrophenyl)quinazolin-4(3H)-one (0.300 g, 49%).

Workup

  1. temperatureAfter heating
  2. temperatureto reflux temperature for 3 hours
  3. concentrationthe mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with H2O
  6. dry with materialbrine, dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography on silica gel
  10. washeluting with 10% to 60% EtOAc in heptane

Sources & evidence

ORD record
ord-acc75f227e3946808c31f9dbff642dbc
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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