Reaktion #165720

Reaktionsgleichung

CH2Cl2

2-amino-5-methylthiazole

4-(2-chloroethyl)-morpholine hydrochloride

Et3N

→

NH4OH

title compound

Ausbeute 88.6%

5-methyl-3-(2-morpholinoethyl)thiazol-2(3H)-imine

Ausbeute 88.6%

Lösungsmittel

CH3OH

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was then cooled to ambient temperature
2. 2
   Sonstigequenched with saturated aqueous NaHCO3 (5 mL)
3. 3
   workup.ADDITIONdiluted with CH2Cl2 (5 mL)
4. 4
   SonstigeThe layers were separated
5. 5
   Extraktionthe aqueous layer was extracted with CH2Cl2 (3×5 mL)
6. 6
   TrocknenThe combined organics were dried over anhydrous Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   Sonstigepurified via column chromatography (SiO2, 10% CH3OH in EtOAc

Vorschrift

A mixture of 2-amino-5-methylthiazole (1.0 g, 8.8 mmol), 4-(2-chloroethyl)-morpholine hydrochloride (1.7 g, 9.2 mmol) and Et3N (3.7 mL, 26 mmol) in DMF (5 mL) was warmed to 80° C. and was allowed to stir for 24 h. The mixture was then cooled to ambient temperature, quenched with saturated aqueous NaHCO3 (5 mL), and diluted with CH2Cl2 (5 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×5 mL). The combined organics were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via column chromatography (SiO2, 10% CH3OH in EtOAc then 9:1:0.1 CH2Cl2:CH3OH:NH4OH) to give the title compound (0.88 g, 3.9 mmol, 44% yield). MS (DCI/NH3) m/z 228 (M+H)+.

Quelle