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

HRID 505596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505596
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-67dafb13fa44418ea8e3092aa0723c25
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781473B2

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