Benzyl Alcohol → 2,4-Bisbenzyloxy-6-methoxyquinazoline
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]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
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
- temperatureThe obtained mixture was heated
- temperatureunder reflux for several hours
- extractionThe obtained mixture was extracted with chloroform
- dry with materialthe organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- distillationThe filtrate was distilled under a reduced pressure
- customto remove the solvent
- customThe obtained crystalline residue was recrystallized from chloroform/n-hexane
Sources & evidence
- ORD record
- ord-5c3bc1307dcc4099a140c5cfebfc5409
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06046206
Reaction notes
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