Methyl iodide → HCID 19605774, compound

HRID 1603530Notes

Reaction equation

HRID 1603530 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][NH:17][C:16]2=[O:23].[H-].[Na+].[CH3:26]I>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][N:17]([CH3:26])[C:16]2=[O:23]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 135752750HCID 135752750, compound

Product 1

HCID 19605774HCID 19605774, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

34 mg of 6-[2-(2,5-dimethoxyphenyl)ethyl]-4-quinazolinone are dissolved in 4 ml of dimethylformamide and treated with 4 mg of sodium hydride (80% in mineral oil). After stirring for 30 minutes, 0.1 ml of methyl iodide are added, and stirring is continued for 1 hour. The mixture is poured onto water and extracted with ethyl acetate. The combined organic layers are dried over magnesium sulfate and concentrated in vacuo. Silica gel chromatography (cyclohexane/ethyl acetate=1/2) of the residue gives the title compound as colourless crystals. mp: 83-85°.

Workup

  1. stirringstirring
  2. waitis continued for 1 hour
  3. additionThe mixture is poured onto water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers are dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6890fa1603b4bc6a0f7f32e3b443661
Source dataset
uspto-grants-1999_11
Patent number
US05990116

Reaction notes

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