1,1'-Thiocarbonyldi-2(1H)-pyridone → 4-chloro-1-(4-isothiocyanato-2-methoxy-phenyl)-1H-imidazole

HRID 1803101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1803101
[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][C:8]=2[O:14][CH3:15])[CH:6]=1.[C:16](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:17]>ClCCl>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:13]=[CH:12][C:10]([N:11]=[C:16]=[S:17])=[CH:9][C:8]=2[O:14][CH3:15])[CH:6]=1

Komponenten

4

Edukt 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 580757574-(4-chloro-1H-imidazol-1-yl)-3-methoxyaniline

Produkt 1

HCID 866498874-chloro-1-(4-isothiocyanato-2-methoxy-phenyl)-1H-imidazoleAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Step A (3): Dichloromethane (125 mL) was added to a flask charged with 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyaniline (4.55 g, 20.3 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (4.72 g, 20.3 mmol). The resulting mixture was stirred for 24 h at rt. The crude reaction mixture was concentrated and the crude products were purified using silica gel chromatography to afford 4-chloro-1-(4-isothiocyanato-2-methoxy-phenyl)-1H-imidazole (4.28 g, 79% yield) as a white solid. LC-MS (M+H)+ 266.0. 1H NMR (500 MHz, chloroform-d) δ ppm 7.60 (d, J=1.53 Hz, 1 H) 7.24 (d, J=8.24 Hz, 1 H) 7.09 (d, J=1.83 Hz, 1 H) 6.93 (dd, J=8.24, 2.14 Hz, 1 H) 6.89 (d, J=2.14 Hz, 1 H) 3.88 (s, 3 H).

Aufarbeitung

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. customthe crude products were purified

Quellen und Nachweise

ORD-Eintrag
ord-24bba4721837498ba6b1d791a774cdcd
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349880B2

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