N,N-Dimethylaniline → 4(1H)-Quinazolinone

HRID 2244097Notes

Reaction equation

HRID 2244097 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([NH:9][C:10]([NH:12][C:4]2=[CH:3][CH:2]=1)=O)=[O:8].CN(C)C1C=CC=CC=1>P(Cl)(Cl)(Cl)=O>[CH:1]1[CH:2]=[CH:3][C:4]2[N:12]=[CH:10][NH:9][C:7](=[O:8])[C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 949N,N-Dimethylaniline2×HCID 64048Quinazolinedione

Product 1

HCID 1354087534(1H)-QuinazolinoneYield 62%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring suspension of benzoyleneurea 1 (10.0 g, 61.7 mmol) and phosphorus oxychloride (20 ml) in a 500 mL three-necked round-bottomed flask equipped with a magnetic stirrer and reflux condenser, was added N,N-dimethylaniline (7.80 ml, 61.7 mmol) in a single portion. The suspension was heated at reflux for 3 hours and slowly formed a light red solution. The solution was concentrated under reduced pressure and the residue was poured onto ice (100 g). The solution was basified to pH=9.0 using concentrated aqueous sodium bicarbonate solution. The mixture was partitioned between CH2Cl2 and H2O. The organic portion was dried (MgSO4) and evaporated to dryness under reduced pressure. The residue was dissolved in anhydrous THF (75 ml) and cooled to 0° C. Dimethylaniline (67.7 mL, 135 mmol, 2.0 M in THF) was added dropwise, with stirring, over a period of 30 minutes. The solution was then stirred at 0° C. for 1 hour. The solution was concentrated under reduced pressure and the residue was purified by silica gel chromatography using (70% hexanes, 30% ethyl acetate) to obtain 2 (7.90 g, 38.1 mmol, 62% yield) as a white solid.

Workup

  1. customequipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureThe suspension was heated
  4. temperatureat reflux for 3 hours
  5. customslowly formed a light red solution
  6. concentrationThe solution was concentrated under reduced pressure
  7. additionthe residue was poured onto ice (100 g)
  8. customThe mixture was partitioned between CH2Cl2 and H2O
  9. dry with materialThe organic portion was dried (MgSO4)
  10. customevaporated to dryness under reduced pressure
  11. dissolutionThe residue was dissolved in anhydrous THF (75 ml)
  12. stirringThe solution was then stirred at 0° C. for 1 hour
  13. concentrationThe solution was concentrated under reduced pressure
  14. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-660271e684d4436b81eed4f3aa5bcce4
Source dataset
uspto-grants-2010_03
Patent number
US07678802B2

Reaction notes

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