Reaktion #11462

Reaktionsgleichung

water

Phenol

tert-butyl 2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]ethylcarbamate

sodium hydride

→

tert-butyl 2-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]ethylcarbamate

Ausbeute 59.1%

Lösungsmittel

diglyme

diglyme

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperatura chilled
2. 2
   TemperaturThe reaction mixture was cooled
3. 3
   SonstigeThe resulting tan solid was isolated by filtration
4. 4
   Waschenwashed with water
5. 5
   Sonstigedried
6. 6
   Sonstigerecrystallized from isopropanol (25 mL)

Vorschrift

Phenol (1.19 g, 12.6 mmol) was added in portions to a chilled (0° C.) suspension of sodium hydride (0.52 g of 60%, 13.1 mmol) in diglyme (4 mL). The reaction mixture was then stirred for 30 minutes. A warm solution of tert-butyl 2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]ethylcarbamate (3.0 g, 8.70 mmol) in diglyme (6 mL) was added and the reaction mixture was heated at 90° C. overnight. The reaction mixture was cooled and poured slowly into water (100 mL). The resulting tan solid was isolated by filtration, washed with water, dried and then recrystallized from isopropanol (25 mL) to provide 2.07 g of tert-butyl 2-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]ethylcarbamate as white needles. The reaction was repeated using 66.5 g of starting material to provide 50.4 g of product as white needles, m.p. 158–160° C.

Quelle