Hydrogen Peroxide → HCID 178476844, compound

HRID 482443Notes

Reaction equation

HRID 482443 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([C:12]1[CH:26]=[CH:25][C:15]([CH2:16][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[CH:14][CH:13]=1)=O)#[N:2].[OH:27]O.[OH-].[Na+]>C1COCC1.[Cl-].[Na+].O>[OH:27][C:1]1[C:3]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:9]=[C:10]([C:12]2[CH:26]=[CH:25][C:15]([CH2:16][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[CH:14][CH:13]=2)[N:2]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 10738021diethyl 4-[N-(2-cyanophenyl)carbamoyl]benzylphosphonate

Product 1

HCID 178476844HCID 178476844, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Diethyl 4-[N-(2-cyanophenyl)carbamoyl]benzylphosphonate (11.2 g) was dissolved in 100 ml of THF and cooled with ice water. After adding 50 ml of a 30% hydrogen peroxide aqueous solution containing 1.2 g of sodium hydroxide dropwise, the reaction mixture was stirred at room temperature for 16 hours. Saturated brine (50 ml) was added, and the reaction mixture was extracted with chloroform. The chloroform layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was dissolved in 150 ml of ethanol and 20 ml of a 2N sodium hydroxide solution and stirred at room temperature for 6 hours. Saturated brine (150 ml) was added, and the reaction mixture was extracted with chloroform. The chloroform layer was dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was recrystallized with methylene chloride-diethyl ether to give 5.9 g of diethyl 4-(4-hydroxyquinazolin-2-yl)benzylphosphonate as colorless crystals.

Workup

  1. extractionthe reaction mixture was extracted with chloroform
  2. dry with materialThe chloroform layer was dried over magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in 150 ml of ethanol
  5. stirring20 ml of a 2N sodium hydroxide solution and stirred at room temperature for 6 hours
  6. additionSaturated brine (150 ml) was added
  7. extractionthe reaction mixture was extracted with chloroform
  8. dry with materialThe chloroform layer was dried over magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was recrystallized with methylene chloride-diethyl ether

Sources & evidence

ORD record
ord-d5568d12ef1242a6b07d99407bf7fd13
Source dataset
uspto-grants-1998_08
Patent number
US05798344

Reaction notes

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