Dimethyl Sulfoxide → HCID 86584677, compound

HRID 279466Notes

Reaction equation

HRID 279466 reaction equation
CS(C)=O.[C-:5]#[N:6].[Na+].[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:13]([CH:19]=1)[C:14](Cl)=[N:15][O:16][CH3:17]>C(OCC)(=O)C>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:13]([C:14](=[N:15][O:16][CH3:17])[C:5]#[N:6])[CH:19]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 54003563HCID 54003563, compound

Product 1

HCID 86584677HCID 86584677, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Dimethyl sulfoxide (3 ml) and 95% sodium cyanide (0.31 g, 6 mmol) were added to 5-chloro-2-(4-chlorobenzyloxy)-α-methoxyiminobenzyl chloride (1.03 g, 3 mmol), and the mixture was stirred at 100° C. for 4 hours. After completion of the reaction, ethyl acetate (150 ml) was added, and the mixture was washed with saturated brine (100 ml) twice. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 5-chloro-2-(4-chlorobenzyloxy)-α-methoxyiminophenylacetonitrile (0.92 g, 91.5%) as crystals.

Workup

  1. additionwas added
  2. washthe mixture was washed with saturated brine (100 ml) twice
  3. dry with materialThe ethyl acetate layer was dried 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-0de047bf03294440a55b1da8dcb8f883
Source dataset
uspto-grants-2002_03
Patent number
US06362212B1

Reaction notes

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