Dimethyl Sulfate → HCID 54390956, compound

HRID 1756747Notes

Reaction equation

HRID 1756747 reaction equation
[OH-].[Na+].[N:3]([O:5][CH2:6]CCC)=O.[CH3:10][C:11]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:12]=1[O:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[CH2:17][C:18]#[N:19].S(OC)(OC)(=O)=O>O.C1(C)C=CC=CC=1.CC(C)=O>[CH3:10][C:11]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:12]=1[O:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([C:18]#[N:19])=[N:3][O:5][CH3:6]

Participants

8

Reactant 4

HCID 6497Dimethyl SulfateHCID 10996Butyl nitriteHCID 14798Sodium Hydroxide2×HCID 11118528HCID 11118528, compound

Product 1

HCID 54390956HCID 54390956, compoundYield 87.7%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

95% Sodium hydroxide (0.32 g, 7.5 mmol), acetone (5 ml) and butyl nitrite (0.62 g, 6 mmol) were added to 2-(2,5dimethylphenoxymethyl)benzyl cyanide (1.26 g, 5 mmol). The mixture was stirred at room temperature for 2 hours. Dimethyl sulfate (0.95 g, 7.5 mmol) was added, and the mixture was stirred under ice-cooling for 10 minutes and at room temperature for 1 hour. After completion of the reaction, toluene (10 ml) and 1N aqueous sodium hydroxide solution (10 ml) were added, and the mixture was stirred at room temperature for 1 hour. After stirring, water (100 ml) was added. The mixture was extracted with ether (100 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminobenzyl cyanide (1.29 g, Yield: 87.6%, E/Z=13/87 ).

Workup

  1. stirringthe mixture was stirred under ice-
  2. temperaturecooling for 10 minutes and at room temperature for 1 hour
  3. additionwere added
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. stirringAfter stirring
  6. extractionThe mixture was extracted with ether (100 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-41b9648fd6c2402eaecd0d8f2cb5d750
Source dataset
uspto-grants-1995_08
Patent number
US05442063

Reaction notes

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