Reaktion #576407

Reaktionsgleichung

HCl

sarcosine ethyl ester

2,6-dichloropyridin-4-yl isocyanate

→

titled compound

Ausbeute 155.4%

3-(2,6-Dichloropyridin-4-yl)-1-methyl-imidazolidine-2,4-dione

Ausbeute 155.4%

Lösungsmittel

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe formed triethylamine hydrochloride was filtered off
2. 2
   Waschenrinsed with DCM (20 ml)
3. 3
   SonstigeThe filtrate was transferred into a 3-necked round bottom flask
4. 4
   Sonstigethe inner temperature below 10° C
5. 5
   Temperaturthe reaction mixture was refluxed for 10 h
6. 6
   TemperaturAfter cooling to RT
7. 7
   Waschenthe solution was washed with brine
8. 8
   Trocknendried over MgSO4
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe obtained amorphous solid was chromatographed over silica gel (eluent: cyclohexane/EtOAc 80/20 to 50/50)

Vorschrift

TEA (7.2 ml, 51 mmol) was added to a suspension of the HCl salt of sarcosine ethyl ester (3.4 g, 24.5 mmol) in dry DCM (80 ml). The formed triethylamine hydrochloride was filtered off and rinsed with DCM (20 ml). The filtrate was transferred into a 3-necked round bottom flask and cooled to 5° C. A solution of 2,6-dichloropyridin-4-yl isocyanate (10 g, 53 mmol) in DCM (25 ml) was added dropwise over 10 min while keeping the inner temperature below 10° C. After 96 h at RT, the reaction mixture was refluxed for 10 h. After cooling to RT, the solution was washed with brine, dried over MgSO4 and concentrated. The obtained amorphous solid was chromatographed over silica gel (eluent: cyclohexane/EtOAc 80/20 to 50/50) to yield the above titled compound as a white solid (9.9 g). mp=134° C. 1H NMR (CDCl3): 7.75 (2H, s), 4.07 (2H, s), 3.10 (3H, s).

Quelle