Reaktion #956701

Reaktionsgleichung

sodium hydroxide

tin (II) chloride

2-Methoxy-N-(2-methoxy-6-nitrophenyl)acetamide

→

4-methoxy-2-(methoxymethyl)-1H-benzo[d]imidazole

Ausbeute 32.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith heating
2. 2
   Temperaturunder reflux for 1 hr
3. 3
   FiltrationThe mixture was filtered through celite
4. 4
   Extraktionthe solution was extracted 3 times with ethyl acetate
5. 5
   TrocknenThe combined organic layers were dried over anhydrous magnesium sulfate
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   workup.STIRRINGisopropyl alcohol (3 mL), and stirred at room temperature for 1 hr
8. 8
   Filtrationsuction filtered
9. 9
   Sonstigethe obtained solid was dried under reduced pressure

Vorschrift

[step 2] 2-Methoxy-N-(2-methoxy-6-nitrophenyl)acetamide (5.4 g, 22.5 mmol) obtained in step 1 was dissolved in ethanol (45 mL), tin (II) chloride.2 hydrate (24.4 g, 108 mmol) was added, and the mixture was stirred with heating under reflux for 1 hr. After cooling to room temperature, 4 mol/L aqueous sodium hydroxide solution was added to the mixture. The mixture was filtered through celite, and the solution was extracted 3 times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained brown oil (3.7 g) was suspended in diisopropyl ether (30 mL) and isopropyl alcohol (3 mL), and stirred at room temperature for 1 hr. The suspension was suction filtered, and the obtained solid was dried under reduced pressure to give 4-methoxy-2-(methoxymethyl)-1H-benzo[d]imidazole (1.38 g, 32%).

Quelle