Methyl iodide → HCID 57663228, compound

HRID 548723Notes

Reaction equation

HRID 548723 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:16]=[CH:15][C:7]2[C:8](=[O:14])[NH:9][C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[CH:5]=1.[CH3:17]I>C1COCC1>[F:3][C:4]1[CH:16]=[CH:15][C:7]2[C:8](=[O:14])[N:9]([CH3:17])[C:10]([CH3:12])([CH3:13])[O:11][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57663162HCID 57663162, compound

Product 1

HCID 57663228HCID 57663228, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in oil) (112 mg, 2.82 mmol) was added to a solution of 7-fluoro-2,2-dimethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one (0.5 g, 2.56 mmol) in THF (10 mL) at 0° C., under argon then the mixture allowed to warm to RT and methyl iodide (0.18 mL, 2.82 mmol) added. The reaction was stirred at RT for 24 hours, poured into ice/water (50 mL) and extracted into ethyl acetate (50 mL). The organic layer was washed with brine (50 mL), dried (MgSO4), and the solvent removed in vacuo to give a yellow oil which was chromatographed on silica, eluting with 30-60% ethyl acetate in isohexane, to give the desired compound as a colourless oil (0.36 g). 1H NMR δ (CDCl3): 1.65 (s, 6H), 3.08 (s, 3H), 6.61 (dd, 1H), 6.75-6.80 (m, 1H), 7.93-7.96 (m, 1H); m/z 210 (M+H)+

Workup

  1. extractionextracted into ethyl acetate (50 mL)
  2. washThe organic layer was washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto give a yellow oil which
  6. customwas chromatographed on silica
  7. washeluting with 30-60% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-4ee79dae82ac4f31ba8a61995958de7d
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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