反応 #165720

反応方程式

CH2Cl2

2-amino-5-methylthiazole

4-(2-chloroethyl)-morpholine hydrochloride

Et3N

→

NH4OH

title compound

収率 88.6%

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

収率 88.6%

溶媒

CH3OH

DMF

反応条件

後処理

1. 1
   温度The mixture was then cooled to ambient temperature
2. 2
   その他quenched with saturated aqueous NaHCO3 (5 mL)
3. 3
   workup.ADDITIONdiluted with CH2Cl2 (5 mL)
4. 4
   その他The layers were separated
5. 5
   抽出the aqueous layer was extracted with CH2Cl2 (3×5 mL)
6. 6
   乾燥The combined organics were dried over anhydrous Na2SO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他purified via column chromatography (SiO2, 10% CH3OH in EtOAc

実験手順

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)+.

出典