Iodoethane → HCID 15908876, compound

HRID 2270161Notes

Reaction equation

HRID 2270161 reaction equation
[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([F:21])=[C:15]([F:20])[CH:16]=2)[NH:11][C:10]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:25](I)[CH3:26]>CN(C=O)C>[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([F:21])=[C:15]([F:20])[CH:16]=2)[N:11]([CH2:25][CH3:26])[C:10]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 15908875HCID 15908875, compound

Product 1

HCID 15908876HCID 15908876, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 3-benzyloxy-6,7-difluoro-1H-quinazoline-2,4-dione (Example B, 3.0 g, 9.9 mmol) in 100 mL of DMF was added to a suspension of sodium hydride (0.47 g, 11.8 mmol) in 40 mL of DMF and stirred for 30 minutes. Ethyl iodide (7.9 mL, 99 mmol) was added, and the mixture was warmed to 50° 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, brine, and dried over magnesium sulfate. The solution was concentrated to give 3.2 g of the title compound as a solid, mp 133-135° C.

Workup

  1. customThe reaction was quenched with 1 mL of water
  2. concentrationconcentrated to an oil
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-60d4b0779c584649a795fdf75c4d0024
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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