Triethylamine → 3-(Cyanoamino)phenyl cyanate

Temperature

0 °C

55 g (0.5 mol) of m-aminophenol are dissolved in 500 ml of isopropanol in a 1 liter three-necked flask equipped with a stirrer, thermometer and dropping funnel. A solution, precooled to 0° C, of 55.0 ml (1.10 mol) of cyanogen chloride in 50 ml of isopropanol is slowly added dropwise with stirring to the resulting solution at a temperature of 0° C. On completion of the reaction, a solution of 106 g (1.05 mol) of triethylamine in 50 ml of isopropanol is pumped in below the surface at 0° C by means of a metering pump. The reaction mixture is then stirred for 2 hours at room temperature. The product which precipitates is filtered off under suction, washed with 50 ml of isopropanol, subsequently taken up in 500 ml of dichloroethane and the triethyl ammonium chloride is extracted with water. Removal of the solvent by distillation at room temperature leaves the crude m-cyanatophenyl cyanamide which, in the IR-spectrum, shows two absorption bands characteristic of the cyanamide and the cyanate group in the region of 4.5 μ.

1. customequipped with a stirrer
2. additionis slowly added dropwise
3. customOn completion of the reaction
4. customis pumped in below the surface at 0° C by means of a metering pump
5. stirringThe reaction mixture is then stirred for 2 hours at room temperature
6. customThe product which precipitates
7. filtrationis filtered off under suction
8. washwashed with 50 ml of isopropanol
9. extractionthe triethyl ammonium chloride is extracted with water
10. customRemoval of the solvent
11. distillationby distillation at room temperature

ORD record

ord-4eda93997bd740e1bfeeac85e061e64e

Source dataset

uspto-grants-1977_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04059567