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

HRID 1008339Notes

Reaction equation

HRID 1008339 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]=[CH:19][NH:18][C:17]2=O)[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:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]=[CH:19][N:18]=[C:17]2[Cl:3])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 1354970176-(Benzyloxy)-7-methoxyquinazolin-4(1H)-one

Product 1

HCID 114265806-(Benzyloxy)-4-chloro-7-methoxyquinazolineYield 72%

Procedure

Phosphorus oxychloride (3.1 ml) was added to 6-(benzyloxy)-7-methoxy-3,4-dihydro-4-quinazolinone (3.5 g) and diisopropylethylamine (11.5 ml). The mixture was refluxed for 20 min. The reaction solution was cooled to room temperature, and a 10% aqueous sodium hydroxide solution was then added to the cooled 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 2.9 g (yield 72%) 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-82ee696a400b4a85a000176fe8e50fb1
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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