Sodium Hydroxide → 7-(Benzyloxy)-4-chloro-6-methoxyquinazoline

HRID 1008337Notes

Reaction equation

HRID 1008337 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([O:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18](=O)[NH:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[O:25][CH3:26])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(C(C)C)CC)(C)C.[OH-].[Na+]>>[CH2:6]([O:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([Cl:3])=[N:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[O:25][CH3:26])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 1354047187-Benzyloxy-6-methoxy-3H-quinazolin-4-one

Product 1

HCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazolineYield 99%

Procedure

Phosphorus oxychloride (515 ml) was added to 7-(benzyloxy)-6-methoxy-3,4-dihydro-4-quinazolinone (400 mg) and diisopropylethylamine (0.3 ml), and the mixture was refluxed for 20 min. The reaction solution was cooled to room temperature. A 10% aqueous sodium hydroxide solution was then added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over sodium sulfate. The organic layer was filtered, and the solvent was then removed by distillation under the reduced pressure. The residue was dried through a vacuum pump to give 420 mg (yield 99%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 20 min
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationThe organic layer was filtered
  5. customthe solvent was then removed by distillation under the reduced pressure
  6. customThe residue was dried through a vacuum pump

Sources & evidence

ORD record
ord-039df9c8e9594d4db9f1692e3deb1e5f
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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