4-Chloro-3-nitrotoluene → N-[3-Fluoro-4-(4-methyl-2-nitro-phenylsulfanyl)-phenyl]-acetamide

HRID 2197746Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2197746
[F:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].ClC1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23]

Komponenten

5

Edukt 2

HCID 69764-Chloro-3-nitrotolueneHCID 68459196N-(3-Fluoro-4-methylsulfanyl-phenyl)-acetamide

Produkt 1

HCID 68460909N-[3-Fluoro-4-(4-methyl-2-nitro-phenylsulfanyl)-phenyl]-acetamideAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The product from Example 39c (1.00 g, 5.0 mmol) and t-BuSNa (1.88 g, 15.1 mmol) in anhydrous DMF (10 mL) was heated at 160° C. for 4 hours under N2 flow, and then cooled to room temperature. To the reaction mixture was added 1-chloro-4-methyl-2-nitrobenzene (2.36 mL, 17.6 mmol) at room temperature and then the mixture was heated at 80° C. for 4 hours under N2 flow. The mixture was diluted with H2O and then extracted with EtOAc. The extract washed with H2O and brine, dried over MgSO4, and evaporated. The residue was purified by silica gel column chromatography eluting with 2:1 EtOAc/hexane to give the title compound as yellow crystals (1.04 g, 65%).

Aufarbeitung

  1. temperaturethe mixture was heated at 80° C. for 4 hours under N2 flow
  2. extractionextracted with EtOAc
  3. washThe extract washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 2:1 EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-d9a01fe429be4c10a52c2567f29d654a
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338605B2

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