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

HRID 330254

반응식

HRID 330254 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3349346de6f546d2869c6139ab9dacd7
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04895862

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