Water → 2-fluoro-5-methoxy-4-(1-methyl-1H-benzimidazol-2-ylmethoxy)-benzaldehyde

HRID 253474

Reaktionsgleichung

Reaktionsgleichung von HRID 253474
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].Cl[CH2:16][C:17]1[N:21]([CH3:22])[C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[N:18]=1.O>CN(C)C(=O)C>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:16][C:17]2[N:21]([CH3:22])[C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[N:18]=2)[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2480442-(Chloromethyl)-1-methylbenzimidazoleHCID 5981552-Fluoro-4-hydroxy-5-methoxybenzaldehyde

Produkt 1

HCID 598038732-fluoro-5-methoxy-4-(1-methyl-1H-benzimidazol-2-ylmethoxy)-benzaldehydeAusbeute 267,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-fluoro-4-hydroxy-5-methoxy-benzaldehyde (39, 3.0 g, 5 mmol) in N,N-dimethylacetamide (120 mL) was added sodium hydride (60% dispersion in mineral oil, 0.8 g, 19 mmol) portion wise. After the addition was complete, the reaction was stirred for 30 minutes after which 2-chloromethyl-1-methyl-1H-benzoimidazole (212, 2.9 g, 16 mmol) was added and then heated at 80° C. overnight. The reaction mixture was then poured into water (1 L) with stirring and the precipitated solid was filtered, washed with water and dried to give the desired compound (213, 4.2 g, 84% yield).

Aufarbeitung

  1. additionAfter the addition
  2. additionwas added
  3. filtrationthe precipitated solid was filtered
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5745c0bd33554da4aea5d3f33ddc96d3
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872018B2

Verknüpfte Notizen

Wird geladen…