Reaktion #987158

Reaktionsgleichung

water acetonitrile

water acetonitrile

sodium hydride

5,5-dimethyl-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione

2-ethyl-4-(bromomethyl)pyridine

→

5,5-dimethyl-1-(2-ethylpyrid-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione

Ausbeute 66.3%

Lösungsmittel

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONfollowed by addition of ice-cold water
2. 2
   Sonstigeafter reaction for 10 minutes
3. 3
   WaschenThe elution
4. 4
   workup.WAITis performed with a mixture (water/acetonitrile) (95/5) (v/v) over 20 minutes
5. 5
   workup.WAITfollowed by a linear gradient of from 5% to 95% acetonitrile over 60 minutes, at a flow rate of 10 ml/minute
6. 6
   EinengenThe fractions between 750 and 790 ml are concentrated under reduced pressure

Vorschrift

0.009 g of sodium hydride is added to a solution of 0.064 g of 5,5-dimethyl-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione in 1 ml of anhydrous dimethylformamide, under an inert atmosphere of argon, at a temperature in the region of 20° C. Stirring is continued at this temperature for 30 minutes. A solution of 0.062 g of 2-ethyl-4-(bromomethyl)pyridine in 0.5 ml of anhydrous dimethylformamide is added, followed by addition of ice-cold water after reaction for 10 minutes. The reaction mixture is placed on a cartridge 27 mm in diameter packed with 25 g of octadecyl-grafted 40-60 μm silica conditioned successively with the mixture (water/acetonitrile) (5/95) (v/v) and then with the mixture (water/acetonitrile) (95/5) (v/v). The elution is performed with a mixture (water/acetonitrile) (95/5) (v/v) over 20 minutes, followed by a linear gradient of from 5% to 95% acetonitrile over 60 minutes, at a flow rate of 10 ml/minute. The fractions between 750 and 790 ml are concentrated under reduced pressure. 0.06 g of 5,5-dimethyl-1-(2-ethylpyrid-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione is thus obtained, the characteristics of which product are as follows:

Quelle