Phosphorus oxychloride → HCID 18796639, compound

HRID 1900696Notes

Reaction equation

HRID 1900696 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([O:13][CH2:14][C:15]1[NH:24][C:23](=O)[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:26][CH3:27])[CH:21]=2)[N:16]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(#N)C>[CH2:6]([O:13][CH2:14][C:15]1[N:24]=[C:23]([Cl:3])[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:26][CH3:27])[CH:21]=2)[N:16]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135815062HCID 135815062, compound

Product 1

HCID 18796639HCID 18796639, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

30 ml of phosphorus oxychloride was added to a suspension of 1.50 g (5.06 mmol) of 2-benzyloxymethyl-6-methoxyquinazolin-4(3H)-one in 75 ml of acetonitrile. The obtained mixture was heated under reflux. After one hour, the reaction mixture was distilled under a reduced pressure to remove the solvent and the obtained residue was dissolved in chloroform. The obtained solution was washed with a saturated aqueous solution of sodium hydrogen-carbonate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under a reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to give 1.10 g of the title compound as a yellow crystal.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux
  3. distillationthe reaction mixture was distilled under a reduced pressure
  4. customto remove the solvent
  5. dissolutionthe obtained residue was dissolved in chloroform
  6. washThe obtained solution was washed with a saturated aqueous solution of sodium hydrogen-carbonate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. distillationThe filtrate was distilled under a reduced pressure
  10. customto remove the solvent
  11. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-3635e5960d894f97a46d61e91733c28c
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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