Chloride → 2-(Hydroxyimino)-2-phenylacetonitrile

HRID 1155483Notes

Reaction equation

HRID 1155483 reaction equation
[CH:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCl.[C-:12]#[N:13].[Na+].[Cl-].[OH-].[Na+].Cl>C(Cl)(Cl)(Cl)Cl.O>[N:8](=[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:12]#[N:13])[OH:9]

Participants

9

Reactant 6

HCID 312ChlorideHCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 12143(Z)-Benzaldehyde oximeHCID 14798Sodium HydroxideHCID 24526Chlorine

Product 1

HCID 699982-(Hydroxyimino)-2-phenylacetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent3×

Procedure

To 9.07 g (75 mmol) of benzaldoxime in 25 ml of carbon tetrachloride is added dropwise, at 5°, a solution of 45 ml of carbon tetrachloride saturated with 5.6 g (79 mmol) of chlorine gas. The mixture is stirred for 1 hourin an ice bath and then excess chlorine is removed by vacuum. A saturated solution of 7.35 g (150 mmol) of sodium cyanide in water is added dropwise, at 0°, to the thus-prepared phenhydroxamoyl chloride (I; R is phenyl, X is chloro). The mixture is stirred for 2 hours as it is allowed to warm to RT. An excess of aqueous sodium hydroxide is added to dissolve the product into the aqueous solution and then the carbon tetrachloride layer is discarded. The aqueous layer is acidified (HCl) and filtered, and the resulting solid is washed with water and dried to give α-oximinophenylacetonitrile, m.p.=120°-125° (II, R is phenyl).

Workup

  1. customexcess chlorine is removed by vacuum
  2. stirringThe mixture is stirred for 2 hours as it
  3. dissolutionto dissolve the product into the aqueous solution
  4. filtrationfiltered
  5. washthe resulting solid is washed with water
  6. customdried

Sources & evidence

ORD record
ord-d32363865b61483d844c72a2146c2ec4
Source dataset
uspto-grants-1981_11
Patent number
US04302402

Reaction notes

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