反応 #2286372

反応方程式

phosphorus pentasulfide

N-methylcarbamoylmethyl-nicotinamide

pyridine

→

solid

収率 23.0%

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

収率 23.0%

溶媒

toluene

反応条件

後処理

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
   その他the organic layer was removed
6. 6
   workup.ADDITIONThe dark residue was treated with hot saturated aqueous sodium bicarbonate (Na2CO3, 40 mL)
7. 7
   抽出the aqueous layer was extracted with ethyl acetate (2×50 mL)
8. 8
   洗浄The combined organic extracts were washed with brine (50 mL)
9. 9
   乾燥dried over magnesium sulfate (MgSO4)
10. 10
    その他purified by silica gel chromatography (1% methanol in dichloromethane)

実験手順

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).

出典