Water → 4-chloro-6-methylquinazoline

HRID 651631Notes

Reaction equation

HRID 651631 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=O.C(N(CC)CC)C.P(Cl)(Cl)([Cl:22])=O.O>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:22][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH3:1])[CH:3]=2)[N:8]=[CH:7][N:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 1354524426-methylquinazolin-4-ol

Product 1

HCID 9402174-chloro-6-methylquinazoline

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Methyl-3H-quinazolin-4-one (1.1 g, 6.9 mmol) is dissolved in toluene (70 mL). To the solution is added triethyl amine (1.82 g, 18 mmol) and P(O)Cl3 (1.06 g, 6.9 mmol). The solution is heated to reflux. After 3 h, the solution is poured into water (100 mL). The solution is diluted with EtOAc (200 mL). The layers are separated. The organic layer is washed with water, saturated NaHCO3 (aq.) and saturated NaCl (aq.). The organic layer is dried over MgSO4, filtered and concentrated. The title compound is obtained as an oil (0.75 g, 4.2 mmol).

Workup

  1. temperatureThe solution is heated to reflux
  2. customThe layers are separated
  3. washThe organic layer is washed with water, saturated NaHCO3 (aq.) and saturated NaCl (aq.)
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-029e8cce28894ec8801d7129c6782a6c
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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