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

HRID 415966

반응식

HRID 415966 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 24386Thionyl Chloride용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3551856c37c04845b183781b17b550da
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088811B2

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