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

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).

1. filtrationThe formed triethylamine hydrochloride was filtered off
2. washrinsed with DCM (20 ml)
3. customThe filtrate was transferred into a 3-necked round bottom flask
4. customthe inner temperature below 10° C
5. temperaturethe reaction mixture was refluxed for 10 h
6. temperatureAfter cooling to RT
7. washthe solution was washed with brine
8. dry with materialdried over MgSO4
9. concentrationconcentrated
10. customThe obtained amorphous solid was chromatographed over silica gel (eluent: cyclohexane/EtOAc 80/20 to 50/50)

ORD-Eintrag

ord-a3b0ca61e6a744f0b37d526d63b480b5

Quelldatensatz

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07078420B2