Dimethyl Sulfoxide → HCID 54390956, compound

HRID 279469Notes

Reaction equation

HRID 279469 reaction equation
CS(C)=O.[C-:5]#[N:6].[Na+].[CH3:8][C:9]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:10]=1[O:11][CH2:12][C:13]1[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=1[C:15](Cl)=[N:16][O:17][CH3:18]>CCOCC>[CH3:8][C:9]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:10]=1[O:11][CH2:12][C:13]1[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=1[C:15](=[N:16][O:17][CH3:18])[C:5]#[N:6]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 53783314HCID 53783314, compound

Product 1

HCID 54390956HCID 54390956, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

Dimethyl sulfoxide (2 ml) and 95% sodium cyanide (0.21 g, 0.004 mol) were added to 2-(2,5-dimethylphenoxy-methyl)-α-methoxyiminobenzyl chloride (0.60 g, 0.02 mol), and the mixture was stirred at 110° C. for 2 hours. After completion of the reaction, ether (100 ml) was added, and the mixture was washed with water twice, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetonitrile (0.45 g, 76.4%) as colorless crystals.

Workup

  1. additionwas added
  2. washthe mixture was washed with water twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-7d6717f8ef6847aea740f78d2ab012ef
Source dataset
uspto-grants-2002_03
Patent number
US06362212B1

Reaction notes

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