Ethyl 2-(butylamino)acetate → 1-Butylimidazolidine-2,4-dione

Temperature

50 °C

A quantity of 24.4 g (0.30 mole) of potassium cyanate is added portionwise, at room temperature, to a stirred solution of 31.80 g (0.20 mole) of ethyl N-butylglycinate in 220 mL (0.22 mole) of 1 N hydrochloric acid. The solution is warmed to ca. 90° C. (at ca. 50° C. an oil separates). After 10 minutes at 90° C., concentrated hydrochloric acid (250 mL) is cautiously added over 2 minutes and the resulting solution is heated at 90°100° C. for 1/2 hour. The solution is concentrated at reduced pressure to dryness. The last amounts of water are chased by addition and removal of 3×100 mL of absolute ethanol. The residue is extracted with 400 mL 50% ethanol-methylene chloride. The inorganics are filtered and the filtrate is concentrated to dryness. Trituration of the residue with 100 mL of water and filtration gives pure 1-butylhydantoin in 68% yield; mp 90°92° C.; MS (EI) 156.1 (M+).

1. temperaturethe resulting solution is heated at 90°100° C. for 1/2 hour
2. concentrationThe solution is concentrated at reduced pressure to dryness
3. additionThe last amounts of water are chased by addition and removal of 3×100 mL of absolute ethanol
4. extractionThe residue is extracted with 400 mL 50% ethanol-methylene chloride
5. filtrationThe inorganics are filtered
6. concentrationthe filtrate is concentrated to dryness
7. filtrationTrituration of the residue with 100 mL of water and filtration

ORD record

ord-554b959cff5c441f87b5633507e83fe7

Source dataset

uspto-grants-1995_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05436260