4-Amino-2-(trifluoromethyl)benzonitrile → N-(4-Cyano-3-trifluoromethyl-phenyl)-2-trifluoromethyl-acrylamide

HRID 505596ノート

反応式

HRID 505596 の反応式
[F:1][C:2]([F:9])([F:8])[C:3](=[CH2:7])[C:4](O)=[O:5].[NH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([C:19]([F:22])([F:21])[F:20])[CH:12]=1>S(Cl)(Cl)=O.C(OCC)C>[C:15]([C:14]1[CH:17]=[CH:18][C:11]([NH:10][C:4](=[O:5])[C:3]([C:2]([F:9])([F:8])[F:1])=[CH2:7])=[CH:12][C:13]=1[C:19]([F:20])([F:21])[F:22])#[N:16]

参加物

5

反応物 2

HCID 5221704-Amino-2-(trifluoromethyl)benzonitrileHCID 5876942-(Trifluoromethyl)acrylic acid

生成物 1

HCID 16756176N-(4-Cyano-3-trifluoromethyl-phenyl)-2-trifluoromethyl-acrylamide

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 24386Thionyl Chloride溶媒

実験手順

2-Trifluoromethyl-acrylic acid (36.0 mmoL) in thionyl chloride (2.86 mL) was refluxed for 30 min. Excess thionyl chloride was removed in vacuo to yield a residue. 4-Amino-2-trifluoromethyl-benzonitrile (36.0 mmoL) in diethyl ether (50 mL) was added dropwise to the residue at −40° C. The reaction mixture was slowly warmed to room temperature. The reaction mixture was then partitioned between diethyl ether and water. The diethyl ether layer was washed with saturated sodium bicarbonate, then brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a brown oil. The crude material (the brown oil) was then purified by column chromatography (silica gel, using ethyl acetate as eluent) to yield the title compound as yellow solid.

後処理

  1. customExcess thionyl chloride was removed in vacuo
  2. customto yield a residue
  3. customThe reaction mixture was then partitioned between diethyl ether and water
  4. washThe diethyl ether layer was washed with saturated sodium bicarbonate
  5. dry with materialbrine, dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a brown oil
  9. customThe crude material (the brown oil) was then purified by column chromatography (silica gel, using ethyl acetate as eluent)

出典と根拠

ORDレコード
ord-67dafb13fa44418ea8e3092aa0723c25
出典データセット
uspto-grants-2010_08
特許番号
US07781473B2

反応ノート

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