Methyl iodide → HCID 18665931, compound

HRID 399715Notes

Reaction equation

HRID 399715 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH3:16])[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[O:6]1)=[O:4].[H-].[Na+].[CH3:19]I>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C@:5]1([CH3:16])[C:10](=[O:11])[N:9]([CH3:19])[C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[O:6]1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18944845HCID 18944845, compound

Product 1

HCID 18665931HCID 18665931, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (+)-methyl-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazine-2-carboxylate (0.9 g, 4.1 mmoles) in anhydrous toluene (20 ml), NaH (0.12 g, 5.1 mmoles) and methyl iodide (0.87 g, 6.1 mmoles) were added with stirring and the mixture was heated at reflux temperature for 2 hours. After the completion of the reaction, the toluene solution was washed with water (2×20 ml), 0.1M HCl (2×20 ml) and saturated NaCl solution (20 ml). The solution was dried over MgSO4 and the solvent was evaporated. Thus there were obtained 0.68 g of the title product, which was recrystallized from a mixture of hexane and diethyl ether. The title product was in the form of white crystals, m.p. 76°-78° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 2 hours
  3. customAfter the completion of the reaction
  4. washthe toluene solution was washed with water (2×20 ml), 0.1M HCl (2×20 ml) and saturated NaCl solution (20 ml)
  5. dry with materialThe solution was dried over MgSO4
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8bcc95acc2a54548a12b1326606a502e
Source dataset
uspto-grants-1998_10
Patent number
US05824652

Reaction notes

Loading…