Triethylamine → HCID 68586542, Verbindung

HRID 17532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17532
F[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][C:5]([C:14]#[N:15])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.C(N(CC)CC)C.[CH3:26][N:27]([CH3:33])[C@H:28]1[CH2:32][CH2:31][NH:30][CH2:29]1.C(=O)([O-])O.[Na+]>CS(C)=O.C(OCC)(=O)C>[CH3:26][N:27]([CH3:33])[C@H:28]1[CH2:32][CH2:31][N:30]([C:2]2[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][C:5]([C:14]#[N:15])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=2)[CH2:29]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685844646-Fluoro-4-nitrobiphenyl-3-carbonitrile

Produkt 1

HCID 68586542HCID 68586542, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

6-Fluoro-4-nitrobiphenyl-3-carbonitrile (I-241) (6.0 g, 24.77 mmol) was dissolved in dimethyl sulfoxide (60 ml), and at room temperature, triethylamine (6.9 ml, 49.54 mmol) and (3S)-3-(dimethylamino)pyrrolidine (3.77 ml, 29.73 mmol) were added. After stirring at the same temperature for 19 hours, the reaction liquid was fractionated with ethyl acetate and an aqueous saturated sodium hydrogencarbonate solution. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was subjected to column chromatography with silica gel, and the fraction with chloroform:methanol=95:5 gave the entitled compound (7.90 g, 95%) as an orange powder.

Aufarbeitung

  1. customthe reaction liquid
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe insoluble matter was separated by filtration
  5. customthe solvent was evaporated away

Quellen und Nachweise

ORD-Eintrag
ord-764b17c20c894293869a10be8ba90ac2
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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