Reacción #54195

Ecuación de reacción

N-(2-cyanoethyl)-N-(2-hydroxyethyl)aniline

potassium cyanate

sulfolane

sulfolane

1-bromopropane

→

N-(2-cyanoethyl)-N-[2-(N-propylcarbamoyloxy)ethyl]aniline

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONTo a mixture of 4 g
2. 2
   workup.STIRRINGThe resulting mixture is stirred at 90°-100° C. for three hours
3. 3
   Otrothe resulting layers separated

Procedimiento

To a mixture of 4 g. (.05 mole) of potassium cyanate and 25 ml. of sulfolane at 90° C. are added dropwise 9 ml. (12.3 g, 0.1 mole) of 1-bromopropane over a one-hour period. After 10 minutes of stirring at the same temperature, a solution of 6 g. (0.027 mole) of N-(2-cyanoethyl)-N-(2-hydroxyethyl)aniline in 5 ml. sulfolane is added. The resulting mixture is stirred at 90°-100° C. for three hours and then allowed to cool to 50° C. The mixture is poured into 1 liter of water under agitation, and the resulting layers separated. TLC of the organic layer in 4:1 benzene: acetone shows the absence of starting alcohol with the product of the above formula.

Fuente