Réaction #54194

Équation de réaction

potassium cyanate

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

Bromoethane

bromoethane

sulfolane

sulfolane

→

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

Solvants

water

Conditions de réaction

Traitement

1. 1
   Autrethree-necked round-bottomed flask equipped with thermometer, stirrer
2. 2
   Températurereflux condenser
3. 3
   TempératureThis mixture is heated
4. 4
   Températureheating of the resulting mixture
5. 5
   TempératureThe reaction mixture is cooled to room temperature
6. 6
   workup.STIRRINGThe mixture is agitated for 0.5 hour
7. 7
   Autrethe two resulting layers separated

Mode opératoire

Into a 500 ml. three-necked round-bottomed flask equipped with thermometer, stirrer, reflux condenser, and dropping funnel are placed 40 g. (0.493 mole) of potassium cyanate and 250 ml. of sulfolane (tetrahydrothiophene-1,1-dioxide). This mixture is heated with stirring to 90° C. by means of an oil bath. Bromoethane (95 g., 0.8 mole) is then added dropwise to the mixture over a 1.5 hour period. The temperature of the reaction mixture drops to 75° C. during the addition of bromoethane. A solution of 50 g. (0.228 mole, 86.5%) N-(2-cyanoethyl)-N-(2-hydroxyethyl) aniline in 50 ml. of sulfolane is added, and heating of the resulting mixture is continued at 90° C. for three hours. The reaction mixture is cooled to room temperature and then poured into 2 liters of cold water. The mixture is agitated for 0.5 hour, and the two resulting layers separated. TLC of the organic layer in 4:1 benzene:acetone shows only a trace of starting material. The infrared spectrum of the product of the above formula shows absorptions at 3370, 2250, 1915, 1680, and 596 cm-1.

Source