Water → 4-{N-[1H-imidazol-1-yl]-N-[(6-methoxy-benzothien-3-yl)methyl]amino}benzonitrile

HRID 446167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446167
Cl[CH2:2][C:3]1[C:7]2[CH:8]=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:6]=2[S:5][CH:4]=1.[N:14]1([NH:19][C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)[CH:18]=[CH:17][N:16]=[CH:15]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.[I-].[K+]>[N:14]1([N:19]([C:20]2[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=2)[CH2:2][C:3]2[C:7]3[CH:8]=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:6]=3[S:5][CH:4]=2)[CH:18]=[CH:17][N:16]=[CH:15]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 218271913-Chloromethyl-6-methoxy-benzothiopheneHCID 230181884-[(1H-imidazol-1-yl)amino]benzonitrile

Produkt 1

HCID 694453164-{N-[1H-imidazol-1-yl]-N-[(6-methoxy-benzothien-3-yl)methyl]amino}benzonitrileAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-Chloromethyl-6-methoxy-benzothiophene (12.35 g, 58.06 mmol) was added to a mixture of 4[N-(1H-imidazol-1-yl)amino]benzonitrile (9.72 g, 52.78 mmol), K2CO3 (14.60 g, 105.56 mmol) and potassium iodide (0.10 g, 0.60 mmol) in dry DMF (70 ml) at room temperature. The mixture was then stirred at room temperature overnight and after poured into water and extracted with ethyl acetate, dried over Na2SO4, filtered, and concentrated under vacuum to give the crude product as solid (14.30 g). Flash chromatography on silica gel (toluene/dioxan: 6/4) yielded the expected product (10.50 g, 55%, powder).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto give the crude product as solid (14.30 g)

Quellen und Nachweise

ORD-Eintrag
ord-807e6a9269684bc09ecb1d12b9da681a
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476455B2

Notizen zur Reaktion

Wird geladen…