Benzyl Bromide → HCID 9880589, compound

HRID 1826839Notes

Reaction equation

HRID 1826839 reaction equation
[O:1]([C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:18])[NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[CH2:21]([N:13]1[C:14]2[C:9](=[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:10][NH:11][C:12]1=[O:18])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 22136221HCID 22136221, compound

Product 1

HCID 9880589HCID 9880589, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of 2c above, 5-phenoxy-3,4-dihydro-(1H)-quinazolin-2-one (0.08 g, 0.33 mmol) was dissolved in dimethylformamide (3 mL) and stirred at room temperature under argon. Sodium hydride (0.0084 g, 0.35 mmol) was added and the mixture heated to 55° C. in an oil bath. Gas evolution occurred and a clear solution resulted. Benzyl bromide (0.060 g, 0.35 mmol) was added and the reaction mixture was heated at 55° C. for 1 hour. The solvent was evaporated in vacuo, to give the crude product which was flash chromatographed on silica gel eluted with 0–4% methanol in methylene chloride to give a white amorphous solid. Recrystallization from ethyl acetate hexane gave the title compound as a white crystalline compound. mp 171–173° C.

Workup

  1. temperaturethe mixture heated to 55° C. in an oil bath
  2. customa clear solution resulted
  3. temperaturethe reaction mixture was heated at 55° C. for 1 hour
  4. customThe solvent was evaporated in vacuo
  5. customto give the crude product which
  6. customchromatographed on silica gel
  7. washeluted with 0–4% methanol in methylene chloride
  8. customto give a white amorphous solid
  9. customRecrystallization from ethyl acetate hexane

Sources & evidence

ORD record
ord-12d0f8eb2fe64fe8b8426abda983fbd1
Source dataset
uspto-grants-2006_05
Patent number
US07053099B1

Reaction notes

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