Methyl iodide → HCID 67106673, compound

HRID 1910789Notes

Reaction equation

HRID 1910789 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:19])[CH2:8][O:7][C:6](=[N:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[NH:5]1.I[CH3:21]>C1COCC1>[N+:16]([C:13]1[CH:12]=[CH:11][C:10]([N:9]=[C:6]2[N:5]([CH3:21])[C:4]([CH3:19])([CH3:3])[CH2:8][O:7]2)=[CH:15][CH:14]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178429126HCID 178429126, compound

Product 1

HCID 67106673HCID 67106673, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of sodium hydride (0.2 g of 50% in mineral oil, 4.2 mmol) in THF was added (4,4-dimethyl-oxazolidin-2-ylidene)-(4-nitro-phenyl)-amine (1 g, 4.25 mmol), stirred for 30 min at r.t., followed by addition of iodomethane (0.71 g, 5.0 mmol). After a further 6 hours at r.t. the reaction was quenched with water and extracted with ethyl acetate. The extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue which was purified by column chromatography over silica gel (60-120 mesh) using 15% ethyl acetate/petroleum ether as eluent to give (4-nitro phenyl)-(3,4,4-trimethyl-oxazolidin-2-ylidene)-amine (0.7 g, 66%).

Workup

  1. customAfter a further 6 hours at r.t. the reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a residue which
  7. customwas purified by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-4e2fea706e1e4040a7d34aad9f494954
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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