Dimethylformamide → 2-Phenoxy-alpha-methoxyiminobenzyl cyanide

HRID 1769409Notes

Reaction equation

HRID 1769409 reaction equation
[OH:1][N:2]=[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]#[N:5].[CH3:19]N(C)C=O.C(=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>CCOCC>[CH3:19][O:1][N:2]=[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]#[N:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 853212152-Phenoxy-alpha-hydroxyiminobenzyl cyanide

Product 1

HCID 541653652-Phenoxy-alpha-methoxyiminobenzyl cyanideYield 89.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To α-hydroxyimino-2-phenoxyphenylacetonitrile (a mixture of E- and Z-isomers) (1.19 g, 0.005 mole) were added dried dimethylformamide (10 ml) and potassium carbonate (0.90 g, 0.0065 mole), and dimethylsulfate (0.76 g, 0.006 mole) was added dropwise to the mixture under ice cooling, followed by stirring at room temperature for 1.5 hours. After completion of the reaction, ether (150 ml) was added, followed by washing twice with water (100 ml). The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and then the resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain α-methoxyimino-2-phenoxyphenylacetonitrile (1.13 g, yield: 89.6%) as a colorless oil.

Workup

  1. additionwas added dropwise to the mixture under ice cooling
  2. additionwas added
  3. washby washing twice with water (100 ml)
  4. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-ea1eb65bbcfa4420bcb7e4e82ad3a81b
Source dataset
uspto-grants-1995_01
Patent number
US05380913

Reaction notes

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