Benzyl Alcohol → 2,4-Bisbenzyloxy-6-methoxyquinazoline

HRID 1900651Notes

Reaction equation

HRID 1900651 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:12]1[N:21]=[C:20](Cl)[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:23][CH3:24])[CH:18]=2)[N:13]=1.[OH2:25]>O1CCCC1>[CH2:1]([O:8][C:12]1[N:21]=[C:20]([O:25][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:23][CH3:24])[CH:18]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 99913972,4-Dichloro-6-methoxyquinazoline

Product 1

HCID 187967462,4-Bisbenzyloxy-6-methoxyquinazolineYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3 ml of benzyl alcohol was dissolved in 50 ml of tetrahydrofuran, followed by the addition of 1.0 g of sodium hydride. The obtained mixture was stirred at 40° to 50° C. for 30 minutes, followed by the addition of 2.50 g (0.0109 mol) of 2,4-dichloro-6-methoxyquinazoline. The obtained mixture was heated under reflux for several hours, followed by the addition of water. The obtained mixture was extracted with chloroform and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under a reduced pressure to remove the solvent. The obtained crystalline residue was recrystallized from chloroform/n-hexane to give 3.84 g of the title compound as a yellow crystal.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for several hours
  3. extractionThe obtained mixture was extracted with chloroform
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationThe filtrate was distilled under a reduced pressure
  7. customto remove the solvent
  8. customThe obtained crystalline residue was recrystallized from chloroform/n-hexane

Sources & evidence

ORD record
ord-cf07d4019e9244a3bb7101ec77a0fd97
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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