反应 #2286372

反应方程式

phosphorus pentasulfide

N-methylcarbamoylmethyl-nicotinamide

pyridine

→

solid

收率 23.0%

methyl-(2-pyridin-3-yl-thiazol-5-yl)-amine

收率 23.0%

溶剂

toluene

反应条件

后处理

1. 1
   温度at reflux under nitrogen for 16 h
2. 2
   workup.STIRRINGThe mixture was stirred
3. 3
   温度at reflux under nitrogen for 8 h
4. 4
   温度it was cooled to room temperature
5. 5
   其他the organic layer was removed
6. 6
   workup.ADDITIONThe dark residue was treated with hot saturated aqueous sodium bicarbonate (Na2CO3, 40 mL)
7. 7
   萃取the aqueous layer was extracted with ethyl acetate (2×50 mL)
8. 8
   洗涤The combined organic extracts were washed with brine (50 mL)
9. 9
   干燥dried over magnesium sulfate (MgSO4)
10. 10
    其他purified by silica gel chromatography (1% methanol in dichloromethane)

实验过程

A suspension of phosphorus pentasulfide (1.73 g, 7.8 mmol) and N-methylcarbamoylmethyl-nicotinamide (1 g, 5 mmol) in dry toluene (10 mL) was stirred at reflux under nitrogen for 16 h. The mixture was cooled to room temperature and then dry pyridine (4 mL) was added. The mixture was stirred at reflux under nitrogen for 8 h, then it was cooled to room temperature and the organic layer was removed. The dark residue was treated with hot saturated aqueous sodium bicarbonate (Na2CO3, 40 mL) and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (50 mL), dried over magnesium sulfate (MgSO4), and purified by silica gel chromatography (1% methanol in dichloromethane) to yield a brown amorphous solid (0.22 g, 22%): mp 141-146° C.; 1H NMR (300 MHz, CDCl3) δ 8.97 (d, J=2.4 Hz, 1H), 8.53 (dd, J=5.0, 1.8 Hz, 1H), 8.06 (ddd, J=7.2, 3.3, 0.6 Hz, 1H), 7.31 (ddd, J=5.5, 4.7, 0.5 Hz, 1H), 6.96 (s, 1H), 2.97 (d, J=5.0 Hz, 3H); ESIMS m/z 192 (M+1).

来源