Phosphorus oxychloride → 4,7-Dichloro-2-phenylquinazoline

HRID 493859Notes

Reaction equation

HRID 493859 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[NH:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:9]2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:21]>>[Cl:21][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1354312237-Chloro-2-phenylquinazolin-4(3H)-one

Product 1

HCID 3625064,7-Dichloro-2-phenylquinazoline

Conditions

Temperature
90 °C

Procedure

7-Chloro-2-phenylquinazolin-4(3H)-one (3.11 g, 12.1 mmol) in POCl3 (40 mL) was heated with stirring at 90° C. under N2 for 2 d. The reaction was cooled to rt and evaporated to dryness under high vacuum. The residue was stirred for 30 min at 0° C. under Ar as a suspension in NH3/ i-PrOH (2 M, 45 mL). Later DCM (˜100 mL) was added and stirring was continued for 1 h at rt. Aq NH4OH (conc, 50 mL) was added and layers were separated. The aqueous layer was extracted with DCM (2×). The organic phase was washed (satd NaHCO3, H2O, brine), dried (Na2SO4) and concentrated under reduced pressure to provide the title compound as a light yellow solid; 1H NMR (400 MHz, CD2Cl2) δ 8.56-8.46 (m, 2H), 8.14 (d, J=9.2 Hz, 1H), 8.02 (d, J=2.4 Hz, 1H), 7.56 (dd, J=2.4 Hz, 9.2 Hz, 1H), 7.52-7.45 (m, 3H).

Workup

  1. temperatureThe reaction was cooled to rt
  2. customevaporated to dryness under high vacuum
  3. stirringThe residue was stirred for 30 min at 0° C. under Ar as a suspension in NH3/ i-PrOH (2 M, 45 mL)
  4. additionLater DCM (˜100 mL) was added
  5. stirringstirring
  6. waitwas continued for 1 h at rt
  7. additionAq NH4OH (conc, 50 mL) was added
  8. customlayers were separated
  9. extractionThe aqueous layer was extracted with DCM (2×)
  10. washThe organic phase was washed (satd NaHCO3, H2O, brine)
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d710d870dad746e9a16c2c6b28f80235
Source dataset
uspto-grants-2009_05
Patent number
US07534797B2

Reaction notes

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