Methyl iodide → HCID 131720888, compound

HRID 399713Notes

Reaction equation

HRID 399713 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH3:17])[C:11](=[O:12])[NH:10][C@@H:9]2[CH2:13][CH2:14][CH2:15][CH2:16][C@H:8]2[O:7]1)=[O:5])[CH3:2].[H-].[Na+].[CH3:20]I>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1([CH3:17])[C:11](=[O:12])[N:10]([CH3:20])[C@@H:9]2[CH2:13][CH2:14][CH2:15][CH2:16][C@H:8]2[O:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 131720887HCID 131720887, compound

Product 1

HCID 131720888HCID 131720888, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of trans-ethyl-2-methyl-3-oxo-octahydro-2H-1,4-benzoxazine-2-carboxylate (483 mg, 2 mmoles) in anhydrous toluene (10 ml), NaH (96 mg, 4 mmoles) and methyl iodide (710 mg, 5 mmoles) were added and the mixture was heated for 30 minutes at reflux temperature. After the completion of the reaction, the toluene solution was washed with 1N HCl (10 ml), 1N NaOH (10 ml) and a saturated NaCl solution (10 ml). The solution was dried over MgSO4 and the solvent was evaporated. Thus there were obtained 319 mg (62%) of a yellow product, which was purified by column chromatography (silica gel; chloroform/methanol=9:1). Thus there were obtained 246 mg (48%) of the title compound in the form of a viscous oil.

Workup

  1. temperaturethe mixture was heated for 30 minutes
  2. temperatureat reflux temperature
  3. customAfter the completion of the reaction
  4. washthe toluene solution was washed with 1N HCl (10 ml), 1N NaOH (10 ml)
  5. dry with materialThe solution was dried over MgSO4
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8e51104ac2ad411d8d824542e4ddff24
Source dataset
uspto-grants-1998_10
Patent number
US05824652

Reaction notes

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