Water → Methyl 4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-nitrobenzoate

HRID 874769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 874769
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([C:23]2([C:28]([F:31])([F:30])[F:29])[CH2:27][CH2:26][NH:25][CH2:24]2)[CH:19]=[C:20]([Cl:22])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O>[Cl:22][C:20]1[CH:19]=[C:18]([C:23]2([C:28]([F:31])([F:30])[F:29])[CH2:27][CH2:26][N:25]([C:2]3[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=3)[CH2:24]2)[CH:17]=[C:16]([Cl:15])[CH:21]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 14941412Methyl 4-fluoro-2-nitrobenzoateHCID 582188803-(3,5-Dichlorophenyl)-3-(trifluoromethyl)pyrrolidine

Produkt 1

HCID 58218897Methyl 4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-nitrobenzoateAusbeute 50,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the solution of methyl 4-fluoro-2-nitrobenzoate (1.1 g) and 3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (1.5 g) in 1-methyl-2-pyrrolidinone was added potassium carbonate (1.5 g) and the mixture was heated with stirring at 100° C. for two hours. The mixture was cooled to room temperature and then poured into water, which was then extracted twice with ethyl acetate. The organic layer was combined, which was then washed with water and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was distilled away under the reduced pressure, and the residue was then purified by silica gel chromatography to yield methyl 4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-nitrobenzoate (1.24 g). 1H-NMR (CDCl3) δ: 2.53-2.67 (1H, m), 2.89-2.97 (1H, m), 3.50-3.71 (2H, m), 3.83 (1H, d), 3.85 (3H, s), 4.15 (1H, d), 6.69 (1H, dd), 6.75 (1H, d), 7.26 (2H, d), 7.42 (1H, t), 7.81 (1H, d)

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureThe mixture was cooled to room temperature
  3. extractionwas then extracted twice with ethyl acetate
  4. washwhich was then washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter the drying agent was filtered off
  7. distillationthe solvent was distilled away under the reduced pressure
  8. customthe residue was then purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-af7fb9b9c68c4b62abee9bb92bee4829
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980937B2

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