Tetrahydrofuran → HCID 12715767, Verbindung

HRID 471571Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471571
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:4]=1[C:5]#[N:6].C1COCC1.CCOC(C)=O>CCO.[Pd]>[NH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:3]([S:2][CH3:1])[C:4]=1[C:5]#[N:6]

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 12715768HCID 12715768, Verbindung

Produkt 1

HCID 12715767HCID 12715767, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-(methylthio)-6-nitrobenzonitrile (Example 104c) (1.5 g, 7.73 mmol) in EtOH (150 ml)/THF (50 ml)/EtOAc (50 ml) was added 200 mg of 10% Pd/C. The reaction mixture was hydrogenated on part shaker overnight. After the filtration, the filtered solution was dried down under vacuum, and the residue was purified by chromatography on silica gel eluting with EtOAc/Hexane to give the title compound (79%). 1H NMR (400 MHz, CDCl3) δ 2.51 (s, 3H), 4.47 (s, 2H), 6.53-6.51 (m, 1H), 6.58 (d, J=8.0 Hz, 1H), 7.27-7.21 (m, 1H).

Aufarbeitung

  1. filtrationAfter the filtration
  2. customthe filtered solution was dried down under vacuum
  3. customthe residue was purified by chromatography on silica gel eluting with EtOAc/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-11e73d900d8b40ac94751615a72b0f91
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633186B2

Notizen zur Reaktion

Wird geladen…