تفاعل #2286372

معادلة التفاعل

phosphorus pentasulfide

N-methylcarbamoylmethyl-nicotinamide

pyridine

→

solid

المردود 23.0%

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

المردود 23.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat reflux under nitrogen for 16 h
2. 2
   workup.STIRRINGThe mixture was stirred
3. 3
   درجة الحرارةat reflux under nitrogen for 8 h
4. 4
   درجة الحرارةit was cooled to room temperature
5. 5
   أخرىthe organic layer was removed
6. 6
   workup.ADDITIONThe dark residue was treated with hot saturated aqueous sodium bicarbonate (Na2CO3, 40 mL)
7. 7
   استخلاصthe aqueous layer was extracted with ethyl acetate (2×50 mL)
8. 8
   غسيلThe combined organic extracts were washed with brine (50 mL)
9. 9
   تجفيفdried over magnesium sulfate (MgSO4)
10. 10
    أخرىpurified by silica gel chromatography (1% methanol in dichloromethane)

الإجراء التجريبي

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).

المصدر