m-Trifluoromethylphenylacetonitrile → N'-Hydroxy-2-(3-trifluoromethylphenyl)ethanimidamide

HRID 330254

Reaction equation

HRID 330254 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.Cl.[NH2:15][OH:16].C[O-].[Na+].CO>CO>[OH:16][N:15]=[C:10]([NH2:11])[CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:12])([F:1])[F:13])[CH:4]=1

Participants

5

Reactant 3

HCID 75360m-TrifluoromethylphenylacetonitrileHCID 443297Hydroxyamine hydrochlorideHCID 23694274Sodium methanolate methanol

Product 1

HCID 54224574N'-Hydroxy-2-(3-trifluoromethylphenyl)ethanimidamideYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

m-(Trifluoromethyl)phenylacetonitrile (30.0 g, 0.16 mol) was added to a suspension of hydroxylamine hydrochloride (18.8 g, 0.27 mol), methanol (145 mL) and 25% sodium methoxide/methanol (62 mL, 0.27 mol) at room temperature. The reaction mixture was then heated to reflux for 2 hours, cooled and concentrated in vacuo. The residue was partitioned between methylene chloride and water. The organic layer was separated and dried over magnesium sulfate. The organic layer was concentrated in vacuo. The residue was purified by flash chromatography on silica gel with elution by hexane/ethyl acetate (8/2). The desired product (7.2 g, 21%) was obtained as a white solid, m.p. 91°-92° C.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 2 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between methylene chloride and water
  6. customThe organic layer was separated
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe organic layer was concentrated in vacuo
  9. customThe residue was purified by flash chromatography on silica gel with elution by hexane/ethyl acetate (8/2)

Sources & evidence

ORD record
ord-3349346de6f546d2869c6139ab9dacd7
Source dataset
uspto-grants-1990_01
Patent number
US04895862

Linked notes

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