Реакция #165720

Уравнение реакции

CH2Cl2

2-amino-5-methylthiazole

4-(2-chloroethyl)-morpholine hydrochloride

Et3N

→

NH4OH

title compound

Выход 88.6%

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

Выход 88.6%

Растворители

CH3OH

DMF

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was then cooled to ambient temperature
2. 2
   Другоеquenched with saturated aqueous NaHCO3 (5 mL)
3. 3
   workup.ADDITIONdiluted with CH2Cl2 (5 mL)
4. 4
   ДругоеThe layers were separated
5. 5
   Экстракцияthe aqueous layer was extracted with CH2Cl2 (3×5 mL)
6. 6
   СушкаThe combined organics were dried over anhydrous Na2SO4
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated under reduced pressure
9. 9
   Другоеpurified via column chromatography (SiO2, 10% CH3OH in EtOAc

Методика

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)+.

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