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

HRID 415966

Reaction equation

HRID 415966 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 24386Thionyl ChlorideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3551856c37c04845b183781b17b550da
Source dataset
uspto-grants-2012_01
Patent number
US08088811B2

Linked notes

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