Benzyl Bromide → HCID 22632888, compound

HRID 2270248Notes

Reaction equation

HRID 2270248 reaction equation
[CH2:1]([O:4][N:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([F:17])=[C:11]([F:16])[CH:12]=2)[NH:7][C:6]1=[O:18])[CH:2]=[CH2:3].[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:1]([O:4][N:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([F:17])=[C:11]([F:16])[CH:12]=2)[N:7]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:6]1=[O:18])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 22632985HCID 22632985, compound

Product 1

HCID 22632888HCID 22632888, compoundYield 107.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-allyloxy-6,7-difluoro-1H-quinazoline-2,4-dione (Example Z-3, 0.7 g, 2.8 mmol) in 20 mL of DMF was added to a suspension of sodium hydride (0.12 g, 3.0 mmol) in 15 mL of DMF and stirred for 30 minutes. Benzyl bromide (0.65 mL, 5.5 mmol) was added, and the mixture was stirred at 25° C. for 18 hours. The reaction was quenched with 1 mL of water and concentrated to an oil. The residue was dissolved in chloroform washed with water and brine and dried over magnesium sulfate. The solution was concentrated to give 1.04 g of the title compound as a solid, mp 130-132° C.

Workup

  1. stirringthe mixture was stirred at 25° C. for 18 hours
  2. customThe reaction was quenched with 1 mL of water
  3. concentrationconcentrated to an oil
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-38c8ce550c9d42209175bbb41035e8f4
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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