Methyl iodide → 6-(3,4-dimethoxyphenyl)-3-methyl-3,4,5,6-tetrahydro-2H-1,3-oxazin-2-one

HRID 1068578Notes

Reaction equation

HRID 1068578 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[O:16][C:15](=[O:17])[NH:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].[CH3:20]I>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[O:16][C:15](=[O:17])[N:14]([CH3:20])[CH2:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21189798HCID 21189798, compound

Product 1

HCID 211897636-(3,4-dimethoxyphenyl)-3-methyl-3,4,5,6-tetrahydro-2H-1,3-oxazin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the 6-(3,4-dimethoxyphenyl)-3,4,5,6-tetrahydro-2H-1,3-oxazin-2-one (1.20 g, 5.06 mM) produced in Example 1 in dried N,N-dimethylformamide (30 ml) were added sodium hydride (60%) (0.41 g, 10.12 mM) and methyl iodide (1.44 g, 10.12 mM). The solution was then stirred at room temperature for one night. The reaction solution was carefully poured into ice water, then extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate and the solvent was removed in vacuo to obtain a residue as a brown oil. The residue was purified by flash chromatography (SiO2; eluted by 0.5% methanol/chloroform) to obtain the above-described compound 0.28 g (yield 22.3%) as a colorless solid.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4ffc43d44a494f2cae78518f312d4025
Source dataset
uspto-grants-2001_06
Patent number
US06251897B1

Reaction notes

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