p-Tolunitrile → Quinazoline, 2-(4-methylphenyl)-4-phenyl-

HRID 54900

Reaction equation

HRID 54900 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[CH3:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1.[H-].[Na+]>C1COCC1>[CH3:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]2[N:22]=[C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:3]3[C:2](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:1]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7724p-TolunitrileHCID 24758Sodium hydrideHCID 760802-Aminobenzophenone

Product 1

HCID 9971804Quinazoline, 2-(4-methylphenyl)-4-phenyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A 7.9 g portion of 2-aminobenzophenone, 4.7 g of 4-methylbenzonitrile and 2.0 g of 60% sodium hydride were suspended in 40 ml of THF and heated at 60° C. with stirring for 2 hours. After completion of the reaction, the reaction mixture was allowed to cool and the precipitate was collected by filtration, thus giving 5.7 g of 2-(4-methylphenyl)-4-phenylquinazoline as a crude product. Then 4.4 g of the compound thus obtained, 2.7 g of NBS and 0.2 g of benzoyl peroxide were suspended in 50 ml of carbon tetrachloride and refluxed with heating for 2 hours. The reaction mixture was allowed to cool and 20 ml of diethyl ether was added thereto. The crystals precipitated were separated by filtration. The filtrate was concentrated under reduced pressure. The residue was recrystallized from chloroform-n-hexane to provide 1.9 g of 2-(4-bromomethylphenyl)-4-phenylquinazoline as colorless needles. Then 1.9 g of the crystals thus obtained were suspended in 10 ml of triethyl phosphite and heated with stirring at 130° C. for 2 hours. After completion of the reaction, an excess of triethyl phosphite was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluent: chloroform: n-hexane=1:1) and recrystallized from diethyl ether-n-hexane to provide 0.2 g of the objective compound as colorless needles. Table 1 shows the structure and physical property (melting point) of the compound.

Workup

  1. customAfter completion of the reaction
  2. temperatureto cool
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-d073fcd67a224be79a867f7ec82e9804
Source dataset
uspto-grants-1997_04
Patent number
US05624918

Linked notes

Loading…