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

HRID 489225

Reaktionsgleichung

Cl.C(O[C:5](=[O:9])[CH2:6][NH:7][CH3:8])C.[Cl:10][C:11]1[CH:16]=[C:15]([N:17]=[C:18]=[O:19])[CH:14]=[C:13]([Cl:20])[N:12]=1>C(Cl)Cl>[Cl:10][C:11]1[CH:16]=[C:15]([N:17]2[C:5](=[O:9])[CH2:6][N:7]([CH3:8])[C:18]2=[O:19])[CH:14]=[C:13]([Cl:20])[N:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: 5 °C

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-b2921a2703f44893a9c8b09f9fc8e9c8
Quelldatensatz: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06977267B2

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