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

HRID 330254

Reaktionsgleichung

Reaktionsgleichung von HRID 330254
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3349346de6f546d2869c6139ab9dacd7
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04895862

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