Triethylamine → Itaconamide

Temperatur

5 °C

38.7 grams (0.3 mole) of 2-methylenesuccinamic acid, prepared as described in Example 1, were dissolved in 150 ml of chloroform in a 500 ml. 3-necked round bottom flask equipped with a magnetic stirrer, condenser, drying tube, thermometer, and dropping funnel. The solution was cooled to about 5° C. and a mixture of 41.7 ml. (1 equivalent) of triethylamine and 90 ml. of chloroform was added dropwise over 1/2 hour to the stirring solution. The solution was then cooled to about -45° C. by means of a dry ice-acetone bath. A mixture of 28.5 ml. (1 equivalent) of ethyl chloroformate and 70 ml. of chloroform was added to the solution over a 1/2 hour period, maintaining the solution temperature at about -45° C. The reaction mixture was allowed to stir at -45° C., ±15° C., for an additional 2 hours. The reaction mixture was then transferred to a 1-liter 3-necked round bottom flask fitted with a mechanical stirrer, gas inlet, thermometer, condenser, and drying tube. The solution was maintained at -10° C. while ammonia gas was bubbled into the reaction mixture for 1/2 hour. Additional portions of chloroform, totaling 400 ml., were then added. The reaction mixture was allowed to warm to room temperature and the precipitated product was isolated by suction filtration and air-dried overnight. Repeated recrystallizations from water, methanol/water, and water gave 16.3 gms of itaconamide, a white solid melting at 226°-229° C.

1. custom3-necked round bottom flask equipped with a magnetic stirrer, condenser
2. customdrying tube
3. additiona mixture of 41.7 ml
4. temperatureThe solution was then cooled to about -45° C. by means of a dry ice-acetone bath
5. additionA mixture of 28.5 ml
6. temperaturemaintaining the solution temperature at about -45° C
7. customThe reaction mixture was then transferred to a 1-liter 3-necked round bottom flask
8. customfitted with a mechanical stirrer, gas inlet
9. customthermometer, condenser, and drying tube
10. temperatureThe solution was maintained at -10° C. while ammonia gas
11. customwas bubbled into the reaction mixture for 1/2 hour
12. addition, were then added
13. temperatureto warm to room temperature
14. customthe precipitated product was isolated by suction filtration
15. customair-dried overnight
16. customrecrystallizations from water, methanol/water, and water

ORD-Eintrag

ord-361169dda2f64a96b7fda157f18c27eb

Quelldatensatz

uspto-grants-1984_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04480125