N,N-Dimethylaniline → 4-Chloro-2-methylquinazoline

HRID 2063593Notes

Reaction equation

HRID 2063593 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.P(Cl)(Cl)([Cl:15])=O.CN(C)C1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:15][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([CH3:1])[N:11]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 1354004572-Methyl-4(3H)-quinazolinone

Product 1

HCID 27854214-Chloro-2-methylquinazolineYield 60.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2-methylquinazolin-4(3H)-one (9.2 g, 0.0574 mol) and phosphorous oxychloride (5.8 g, 0.037 mol) in dry toluene (250 ml) was added N,N-dimethyl aniline (13.9 g, 0.14 mol) and the mixture was refluxed for 3 h. The reaction mixture was cooled and washed with water, brine and dried. The solvent was removed under vacuum and the residue was purified by chromatography (silica gel, 60-120 mesh) eluting with pet ether/ethyl acetate (9/1) to afford 4 g (39%) of the titled compound as a solid.

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. temperatureThe reaction mixture was cooled
  3. washwashed with water, brine
  4. customdried
  5. customThe solvent was removed under vacuum
  6. customthe residue was purified by chromatography (silica gel, 60-120 mesh)
  7. washeluting with pet ether/ethyl acetate (9/1)

Sources & evidence

ORD record
ord-5ecc73a36e6943038d7b41741940af79
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Reaction notes

Loading…