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

Temperature

80 °C

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)+.

1. temperatureThe mixture was then cooled to ambient temperature
2. customquenched with saturated aqueous NaHCO3 (5 mL)
3. additiondiluted with CH2Cl2 (5 mL)
4. customThe layers were separated
5. extractionthe aqueous layer was extracted with CH2Cl2 (3×5 mL)
6. dry with materialThe combined organics were dried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. custompurified via column chromatography (SiO2, 10% CH3OH in EtOAc

ORD record

ord-1e19bda0b23f4a049223573c0023ef3a

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841334B2