Methyl 4-(bromomethyl)benzoate → 4-(6-Methoxy-1H-benzoimidazol-2-ylsulfanylmethyl)-benzoic acid methyl ester hydrobromide

HRID 252752

Reaktionsgleichung

Reaktionsgleichung von HRID 252752
[Br:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[CH3:13][O:14][C:15]1[CH:24]=[CH:23][C:18]2[N:19]=[C:20]([SH:22])[NH:21][C:17]=2[CH:16]=1>CN(C=O)C>[BrH:1].[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[CH:12][C:3]([CH2:2][S:22][C:20]2[NH:21][C:17]3[CH:16]=[C:15]([O:14][CH3:13])[CH:24]=[CH:23][C:18]=3[N:19]=2)=[CH:4][CH:5]=1

Komponenten

4

Edukt 2

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 178488032HCID 178488032, Verbindung

Produkt 1

HCID 668939074-(6-Methoxy-1H-benzoimidazol-2-ylsulfanylmethyl)-benzoic acid methyl ester hydrobromideAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-(bromomethyl)benzoate (2.51 g, 11.0 mmol) in DMF (50 mL) was added 5-methoxy-2-benzimidazolethiol (1.98 g, 11.0 mmol). The mixture was stirred at room temperature for 24 h and the solvent was evaporated in vacuo. The residue was suspended in ethyl acetate and the hydrobromide salt was collected by filtration to afford the title compound 234 (4.10 g, 91% yield) as a colorless solid. 1H NMR (DMSO-d6) δ (ppm): 7.90 (d, J=8.2 Hz, 2H), 7.55 (d, J=8.2 Hz, 2H), 7.45 (d, J=8.2 Hz, 1H), 7.03 (s, 1H), 6.94 (d, J=8.2 Hz, 1H), 4.65 (s, 2H), 3.82 (s, 3H), 3.79 (s, 3H).

Aufarbeitung

  1. customthe solvent was evaporated in vacuo
  2. filtrationthe hydrobromide salt was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-59171653810b4dfea2f7a308690709df
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868204B2

Verknüpfte Notizen

Wird geladen…