Methyl iodide → HCID 10658401, compound

HRID 1191667Notes

Reaction equation

HRID 1191667 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([CH3:17])[CH:3]=1.CI.[C:20](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:20][O:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[C:4]([CH3:17])[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 106099214-hydroxy-2,5-dimethyl-phenyl-carbamic acid tert-butyl ester

Product 1

HCID 10658401HCID 10658401, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl (4-hydroxy-2,5-dimethylphenyl)carbamate (1.25 g) and methyl iodide (1.12 g) in N,N-dimethylformamide (10.5 mL) was added potassium carbonate (1.46 g), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (1.32 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-97223304d67e4aa3ac1202e9c3f2792b
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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