Ethanol → HCID 21394062, compound

Temperature

52.5 °C

To a stirred solution of 5-chloro-2-pentanone (87 g., 0.72 mol) in ethanol (750 ml.) contained in a 3-liter round-bottom flask, equipped with reflux condenser and mechanical stirrer was added a solution of ammonium carbonate (214 g.) in water (525 ml) followed by a solution of potassium cyanide (50 g.) in water (265 ml.). The mixture was stirred at 50-55° C. for 2.5 hours, cooled to 5-10° C. and excess carbonate and cyanide was removed by the slow addition of 6 N aqueous hydrochloric acid (approx. 650 ml.) to pH 4 under stirring. The resulting mixture was concentrated to a volume of approximately 1 liter and refrigerated overnight. The crystalline deposit of 5-(3-chloropropyl)-5-methyl-2,4-imidazolidinedione was filtered off, dried and recrystallized from chloroform/petroleum ether (25.1 g., 0.13 mol, 18%) m.p. 119-121° C.

1. customequipped
2. temperaturewith reflux condenser and mechanical stirrer
3. temperaturecooled to 5-10° C.
4. customexcess carbonate and cyanide was removed by the slow addition of 6 N aqueous hydrochloric acid (approx. 650 ml.) to pH 4
5. stirringunder stirring
6. concentrationThe resulting mixture was concentrated to a volume of approximately 1 liter and refrigerated overnight
7. filtrationThe crystalline deposit of 5-(3-chloropropyl)-5-methyl-2,4-imidazolidinedione was filtered off
8. customdried

ORD record

ord-111032c9a5a246968d40918257e2d776

Source dataset

uspto-grants-1977_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04061542