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

HRID 330254

反応式

HRID 330254 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3349346de6f546d2869c6139ab9dacd7
出典データセット
uspto-grants-1990_01
特許番号
US04895862

関連ノート

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